Luminescent material with polycyclic ligand

Abstract

A luminescent material having a polycyclic ligand is disclosed. The luminescent material is a metal complex with a polycyclic ligand, and can be used as a luminescent material in an electroluminescent device. The novel metal complexes can better adjust the light emitting color of a device, lower the driving voltage of the device or keep a low voltage level, improve the efficiency of the device, greatly prolong the service life of the device and provide better performance of the device while keeping very narrow half-peak width. An electroluminescent device and a compound combination are also disclosed.

Description

[0001] This patent application is a divisional application of Chinese invention patent application No. 202110348602.6 with priority dates of April 30, 2020 and November 9, 2020, and the invention name is “A luminescent material with multicyclic ligands”. This application claims the priority of Chinese invention patent application No. 202010362117.X filed on April 30, 2020 and Chinese invention patent application No. 202011219604.7 filed on November 9, 2020, and the entire contents of the Chinese invention patent applications are incorporated herein by reference. Technical Field

[0002] The present invention relates to compounds for organic electronic devices, such as organic light-emitting devices, and more particularly to a metal complex having a polycyclic ligand, and an electroluminescent device and a compound combination comprising the metal complex. Background Art

[0003] Organic electronic devices include but are not limited to the following categories: organic light emitting diodes (OLEDs), organic field effect transistors (O-FETs), organic light emitting transistors (OLETs), organic photovoltaic devices (OPVs), dye-sensitized solar cells (DSSCs), organic optical detectors, organic photoreceptors, organic field effect devices (OFQDs), light emitting electrochemical cells (LECs), organic laser diodes and organic plasmonic light emitting devices.

[0004] In 1987, Tang and Van Slyke of Eastman Kodak reported a double-layer organic electroluminescent device, which included an arylamine hole transport layer and a tri-8-hydroxyquinoline-aluminum layer as an electron transport layer and a light-emitting layer (Applied Physics Letters, 1987, 51 (12): 913-915). Once a bias voltage is applied to the device, green light is emitted from the device. This invention laid the foundation for the development of modern organic light-emitting diodes (OLEDs). The most advanced OLEDs can include multiple layers, such as charge injection and transport layers, charge and exciton blocking layers, and one or more light-emitting layers between the cathode and the anode. Since OLEDs are self-luminous solid-state devices, they offer great potential for display and lighting applications. In addition, the inherent properties of organic materials, such as their flexibility, can make them very suitable for special applications, such as on flexible substrates.

[0005] OLEDs can be divided into three different types based on their light emission mechanism. The OLED invented by Tang and van Slyke is a fluorescent OLED. It uses only singlet light emission. The triplet generated in the device is wasted through non-radiative decay channels. Therefore, the internal quantum efficiency (IQE) of fluorescent OLEDs is only 25%. This limitation has hindered the commercialization of OLEDs. In 1997, Forrest and Thompson reported phosphorescent OLEDs, which used triplet light emission from heavy metals containing complexes as emitters. Therefore, singlet and triplet states can be harvested, achieving 100% IQE. Due to its high efficiency, the discovery and development of phosphorescent OLEDs directly contributed to the commercialization of active matrix OLEDs (AMOLEDs). Recently, Adachi achieved high efficiency through thermally activated delayed fluorescence (TADF) of organic compounds. These emitters have a small singlet-triplet gap, making it possible for excitons to return from triplet to singlet. In TADF devices, triplet excitons can generate singlet excitons through reverse intersystem crossing, resulting in high IQE.

[0006] OLEDs can also be classified into small molecule and polymer OLEDs based on the form of the material used. Small molecules are any organic or organometallic material that is not a polymer. Small molecules can have a large molecular weight as long as they have a precise structure. Dendrimers with well-defined structures are considered small molecules. Polymer OLEDs include conjugated polymers and non-conjugated polymers with pendant luminescent groups. Small molecule OLEDs can become polymer OLEDs if post-polymerization occurs during the manufacturing process.

[0007] There are various OLED manufacturing methods. Small molecule OLEDs are usually manufactured by vacuum thermal evaporation. Polymer OLEDs are manufactured by solution methods such as spin coating, inkjet printing, and nozzle printing. Small molecule OLEDs can also be manufactured by solution methods if the material can be dissolved or dispersed in a solvent.

[0008] The emission color of OLED can be achieved by the structural design of the luminescent material. OLED can include one luminescent layer or multiple luminescent layers to achieve the desired spectrum. Green, yellow and red OLEDs, phosphorescent materials have been successfully commercialized. Blue phosphorescent devices still have problems such as blue unsaturation, short device life and high operating voltage. Commercial full-color OLED displays usually adopt a hybrid strategy, using blue fluorescence and phosphorescent yellow, or red and green. At present, the efficiency of phosphorescent OLEDs decreases rapidly under high brightness conditions, which is still a problem. In addition, it is expected to have a more saturated emission spectrum, higher efficiency and longer device life.

[0009] Phosphorescent metal complexes can be used as phosphorescent doping materials for light-emitting layers and applied in the field of organic electroluminescent lighting or display.

[0010] CN110698518A discloses a method having A metal complex of structure, wherein X is N or P, one of the structures disclosed is: The inventor explored the improvement in material performance brought about by bridging of N and P atoms, but did not notice the improvement in performance brought about by introducing a fused ring system at a specific position of a specific ring.

[0011] CN110790797A discloses a method having A metal complex of structure, one of the structures disclosed is: The inventor explored the improvement in material performance brought about by bridging of O and S atoms, but did not notice the improvement in performance brought about by introducing a fused ring system at a specific position of a specific ring.

[0012] The performance of currently developed metal complexes in electroluminescent devices still has many deficiencies. In order to meet the industry's increasing demands, such as lower voltage, higher device efficiency, luminescent colors in a specific wavelength range, more saturated luminescent colors, and longer device life, the research and development of metal complexes still needs to be deepened. Summary of the invention

[0013] The present invention aims to provide a series of metal complexes with polycyclic ligands to solve at least some of the above problems. The metal complexes can be used as luminescent materials in organic electroluminescent devices. These novel metal complexes can better adjust the luminescent color of the device while maintaining a very narrow half-peak width, reduce the driving voltage of the device or maintain a low voltage level, improve the device efficiency, and significantly increase the device life. This type of novel metal complex can provide better device performance.

[0014] According to one embodiment of the present invention, a metal complex is disclosed, which comprises a ligand L a , L a Having a structure represented by Formula 1:

[0015]

[0016] Wherein, Ring A and Ring B are each independently selected from a five-membered unsaturated carbocyclic ring, an aromatic ring having 6 to 30 carbon atoms, or a heteroaromatic ring having 3 to 30 carbon atoms;

[0017] R i Each occurrence of R is the same or different, indicating mono-, poly- or unsubstituted; ii Each occurrence is identical or different and indicates mono-, poly-, or unsubstituted;

[0018] Y is selected from SiR y R y ,GeR y R y , NR y , P.R. y , O, S or Se;

[0019] When there are two R y When two R y Can be the same or different;

[0020] X1-X2 are selected from CR in the same or different ways each time they appear x or N;

[0021] R, R i , R ii , R x and R y The alkyl radicals are selected, at each occurrence, identically or differently, from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl radicals having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl radicals having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl radicals having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl radicals having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy radicals having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy radicals having 6 to 30 carbon atoms, substituted or unsubstituted substituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amine groups, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;

[0022] Adjacent substituent R i , R x , R y , R and R ii can optionally be linked to form a ring;

[0023] The metal is selected from metals having a relative atomic mass greater than 40.

[0024] According to another embodiment of the present invention, an electroluminescent device is also disclosed, which includes an anode, a cathode, and an organic layer disposed between the anode and the cathode, wherein the organic layer contains a metal complex, and the metal complex contains a ligand L a , L a Having a structure represented by Formula 1:

[0025]

[0026] Wherein, Ring A and Ring B are each independently selected from a five-membered unsaturated carbocyclic ring, an aromatic ring having 6 to 30 carbon atoms, or a heteroaromatic ring having 3 to 30 carbon atoms;

[0027] R i Each occurrence of R is the same or different, indicating mono-, poly- or unsubstituted; ii Each occurrence is identical or different and indicates mono-, poly-, or unsubstituted;

[0028] Y is selected from SiR y R y ,GeR y R y , NR y , P.R. y , O, S or Se;

[0029] When there are two R y When two R y Can be the same or different;

[0030] X1-X2 are selected from CR in the same or different ways each time they appear x or N;

[0031] R, R i , R ii , R x and R y The alkyl radicals are selected, at each occurrence, identically or differently, from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl radicals having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl radicals having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl radicals having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl radicals having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy radicals having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy radicals having 6 to 30 carbon atoms, substituted or unsubstituted substituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amine groups, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;

[0032] Adjacent substituent R i , R x , R y , R and R ii can optionally be linked to form a ring;

[0033] The metal is selected from metals having a relative atomic mass greater than 40.

[0034] According to another embodiment of the present invention, a compound combination is also disclosed, which comprises the metal complex described in the above embodiment.

[0035] The novel metal complex with polycyclic ligand disclosed in the present invention can be used as a luminescent material in an electroluminescent device. These novel metal complexes can better adjust the luminescent color of the device while maintaining a very narrow half-peak width, reduce the driving voltage of the device or maintain a low voltage level, improve the device efficiency, and greatly increase the device life. This type of novel metal complex can provide better device performance. BRIEF DESCRIPTION OF THE DRAWINGS

[0036] Figure 1 is a schematic diagram of an organic light-emitting device that may contain the metal complexes and compound combinations disclosed herein.

[0037] Figure 2 is a schematic diagram of another organic light-emitting device that may contain the metal complex and compound combination disclosed herein.

[0038] Figure 3 is a ligand L exhibiting a metal complex as disclosed herein a The structural formula 1. DETAILED DESCRIPTION

[0039] OLEDs can be manufactured on a variety of substrates, such as glass, plastic, and metal. Figure 1 An organic light-emitting device 100 is shown schematically and non-limitingly. The figure is not necessarily drawn to scale, and some layer structures in the figure may be omitted as needed. The device 100 may include a substrate 101, an anode 110, a hole injection layer 120, a hole transport layer 130, an electron blocking layer 140, a light-emitting layer 150, a hole blocking layer 160, an electron transport layer 170, an electron injection layer 180 and a cathode 190. The device 100 can be manufactured by depositing the described layers in sequence. The properties and functions of each layer and exemplary materials are described in more detail in columns 6-10 of U.S. Patent No. 7,279,704 B2, the entire contents of which are incorporated herein by reference.

[0040] There are more examples of each of these layers. For example, a flexible and transparent substrate-anode combination is disclosed in U.S. Patent No. 5,844,363, which is incorporated by reference in its entirety. An example of a p-doped hole transport layer is m-MTDATA doped with F4-TCNQ at a molar ratio of 50:1, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated by reference in its entirety. An example of a host material is disclosed in U.S. Patent No. 6,303,238 to Thompson et al., which is incorporated by reference in its entirety. An example of an n-doped electron transport layer is BPhen doped with Li at a molar ratio of 1:1, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated by reference in its entirety. U.S. Patent Nos. 5,703,436 and 5,707,745, which are incorporated by reference in their entirety, disclose examples of cathodes including composite cathodes having a thin layer of metal such as Mg:Ag with an overlying transparent, conductive, sputter-deposited ITO layer. The principles and use of barrier layers are described in more detail in U.S. Patent No. 6,097,147 and U.S. Patent Application Publication No. 2003 / 0230980, which are incorporated by reference in their entirety. Examples of injection layers are provided in U.S. Patent Application Publication No. 2004 / 0174116, which is incorporated by reference in its entirety. A description of protective layers can be found in U.S. Patent Application Publication No. 2004 / 0174116, which is incorporated by reference in its entirety.

[0041] The above layered structure is provided by way of non-limiting example. The functions of an OLED can be achieved by combining the various layers described above, or some layers can be omitted entirely. It can also include other layers not explicitly described. Within each layer, a single material or a mixture of multiple materials can be used to achieve optimal performance. Any functional layer can include several sublayers. For example, a light-emitting layer can have two layers of different light-emitting materials to achieve a desired light-emitting spectrum.

[0042] In one embodiment, an OLED may be described as having an "organic layer" disposed between a cathode and an anode. The organic layer may include one or more layers.

[0043] OLED also requires encapsulation layers, such as Figure 2 The organic light emitting device 200 is schematically and non-limitingly shown. Figure 1The difference is that an encapsulation layer 102 may also be included on the cathode 190 to prevent harmful substances from the environment, such as moisture and oxygen. Any material that can provide an encapsulation function can be used as an encapsulation layer, such as glass or an organic-inorganic hybrid layer. The encapsulation layer should be placed directly or indirectly on the outside of the OLED device. Multilayer thin film encapsulation is described in U.S. Patent No. 7,968,146 B2, the entire contents of which are incorporated herein by reference.

[0044] Devices manufactured according to embodiments of the present invention can be incorporated into various consumer products having one or more electronic component modules (or units) of the device. Some examples of these consumer products include flat panel displays, monitors, medical monitors, televisions, billboards, lights for indoor or outdoor lighting and / or signaling, heads-up displays, fully or partially transparent displays, flexible displays, smart phones, tablet computers, tablet phones, wearable devices, smart watches, laptop computers, digital cameras, camcorders, viewfinders, micro displays, 3-D displays, vehicle displays, and taillights.

[0045] The materials and structures described herein may also be used in other organic electronic devices listed above.

[0046] As used herein, "top" means farthest from the substrate, while "bottom" means closest to the substrate. Where a first layer is described as being "disposed" "on" a second layer, the first layer is disposed farther from the substrate. Unless it is specified that the first layer is "in contact with" the second layer, other layers may be present between the first and second layers. For example, a cathode may be described as being "disposed" "on" an anode even though various organic layers are present between the cathode and the anode.

[0047] As used herein, "solution processable" means capable of being dissolved, dispersed or transported in and / or deposited from a liquid medium in the form of a solution or suspension.

[0048] A ligand may be referred to as "photoactive" when it is believed that the ligand directly contributes to the photoactive property of the emissive material. A ligand may be referred to as "ancillary" when it is believed that the ligand does not contribute to the photoactive property of the emissive material, but the ancillary ligand may alter the properties of the photoactive ligand.

[0049] It is believed that the internal quantum efficiency (IQE) of fluorescent OLEDs can exceed the 25% spin-statistical limit through delayed fluorescence. Delayed fluorescence can generally be divided into two types, namely P-type delayed fluorescence and E-type delayed fluorescence. P-type delayed fluorescence is generated by triplet-triplet annihilation (TTA).

[0050] On the other hand, E-type delayed fluorescence does not rely on the collision of two triplets, but on the conversion between triplet and singlet excited state. Compounds capable of producing E-type delayed fluorescence need to have a very small single-triplet gap for the conversion between energy states. Thermal energy can activate the transition from triplet back to singlet. This type of delayed fluorescence is also called thermally activated delayed fluorescence (TADF). The notable feature of TADF is that the delayed component increases with increasing temperature. If the reverse intersystem crossing (RISC) rate is fast enough to minimize the non-radiative decay by triplet, the fraction of backfilling singlet excited state may reach 75%. The total singlet fraction can be 100%, far exceeding the 25% of the spin statistics of the excitons generated by electricity.

[0051] The E-type delayed fluorescence feature can be seen in an exciplex system or a single compound. Without being bound by theory, it is believed that the E-type delayed fluorescence requires the luminescent material to have a small singlet-triplet energy gap (ΔE S-T ). Organic non-metal-containing donor-acceptor luminescent materials may be able to achieve this. The emission of these materials is usually characterized by donor-acceptor charge transfer (CT) type emission. The spatial separation of the HOMO and LUMO in these donor-acceptor type compounds usually produces a small ΔE S-T These states may include CT states. Generally, donor-acceptor light-emitting materials are constructed by linking an electron donor moiety (eg, an amino group or a carbazole derivative) to an electron acceptor moiety (eg, a six-membered aromatic ring containing N).

[0052] Definition of Substituent Terms

[0053] Halogen or halide - as used herein includes fluorine, chlorine, bromine and iodine.

[0054] Alkyl - includes straight chain and branched chain alkyl groups. The alkyl group may be an alkyl group having 1 to 20 carbon atoms, preferably an alkyl group having 1 to 12 carbon atoms, and more preferably an alkyl group having 1 to 6 carbon atoms. Examples of alkyl groups include methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, neopentyl, 1-methylpentyl, 2-methylpentyl, 1-pentylhexyl, 1-butylpentyl, 1-heptyloctyl, 3-methylpentyl. In addition, the alkyl group may be optionally substituted. The carbon in the alkyl chain may be substituted by other heteroatoms. Among the above, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl and neopentyl are preferred.

[0055] Cycloalkyl - as used herein includes cyclic alkyl groups. Preferred cycloalkyl groups are those containing 4 to 10 ring carbon atoms, including cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl, 1-adamantyl, 2-adamantyl, 1-norbornyl, 2-norbornyl, and the like. In addition, cycloalkyl groups may be optionally substituted. The carbons in the ring may be substituted with other heteroatoms.

[0056] Alkenyl - As used herein, linear and branched olefin groups are encompassed. Preferred alkenyl groups are alkenyl groups containing 2 to 15 carbon atoms. Examples of alkenyl groups include vinyl, allyl, 1-butenyl, 2-butenyl, 3-butenyl, 1,3-butadienyl, 1-methylvinyl, styryl, 2,2-diphenylvinyl, 1,2-diphenylvinyl, 1-methylallyl, 1,1-dimethylallyl, 2-methylallyl, 1-phenylallyl, 2-phenylallyl, 3-phenylallyl, 3,3-diphenylallyl, 1,2-dimethylallyl, 1-phenyl-1-butenyl and 3-phenyl-1-butenyl. In addition, alkenyl groups may be optionally substituted.

[0057] Alkynyl - as used herein, encompasses both straight and branched chain alkynyl groups. Preferred alkynyl groups are those containing 2 to 15 carbon atoms. Additionally, alkynyl groups may be optionally substituted.

[0058] Aryl or aromatic group - As used herein, both non-fused and fused systems are contemplated. Preferred aryl groups are those containing 6 to 60 carbon atoms, more preferably 6 to 20 carbon atoms, more preferably 6 to 12 carbon atoms. Examples of aryl groups include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenanthrene, fluorene, pyrene, Perylene and azulene, preferably phenyl, biphenyl, terphenyl, triphenylene, fluorene and naphthalene. In addition, aryl can be optionally substituted. Examples of non-condensed aryl include phenyl, biphenyl-2-yl, biphenyl-3-yl, biphenyl-4-yl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-tolyl, m-tolyl, p-tolyl, p-(2-phenylpropyl)phenyl, 4'-methylbiphenyl, 4"-tert-butyl-p-terphenyl-4-yl, o-cumyl, m-cumyl, p-cumyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, mesityl and m-quadrenyl.

[0059] Heterocyclyl or heterocycle - As used herein, both aromatic and non-aromatic cyclic groups are contemplated. Heteroaryl also refers to heteroaryl. Preferred non-aromatic heterocyclyls are those containing 3 to 7 ring atoms, including at least one heteroatom such as nitrogen, oxygen and sulfur. The heterocyclyl may also be an aromatic heterocyclyl having at least one heteroatom selected from nitrogen, oxygen, sulfur and selenium atoms.

[0060] Heteroaryl - As used herein, non-fused and fused heteroaromatic groups that may contain from 1 to 5 heteroatoms are contemplated. Preferred heteroaryl groups are those containing from 3 to 30 carbon atoms, more preferably from 3 to 20 carbon atoms, more preferably from 3 to 12 carbon atoms. Suitable heteroaryl groups include dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolecarbazole, pyridineindole, pyrrolopyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indazine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, In some embodiments, the heteroaryl group is substituted with 1,2-azaborine, 1,3-azaborine, 1,4-azaborine, borazole and its aza analogs. In some embodiments, the heteroaryl group is substituted with 1,2-azaborine, 1,3-azaborine, 1,4-azaborine, borazole and its aza analogs. In some embodiments, the heteroaryl group is substituted with 1,2-azaborine, 1,3-azaborine, 1,4-azaborine, borazole and its aza analogs. In addition, the heteroaryl group may be optionally substituted.

[0061] Alkoxy - is represented by -O-alkyl. Examples and preferred examples of alkyl are the same as those described above. Examples of alkoxy having 1 to 20 carbon atoms, preferably 1 to 6 carbon atoms, include methoxy, ethoxy, propoxy, butoxy, pentyloxy and hexyloxy. Alkoxy having 3 or more carbon atoms may be linear, cyclic or branched.

[0062] Aryloxy- is represented by -O-aryl or -O-heteroaryl. Examples and preferred examples of aryl and heteroaryl are the same as described above. Examples of aryloxy having 6 to 40 carbon atoms include phenoxy and biphenyloxy.

[0063] Aralkyl - As used herein, an alkyl group having an aryl substituent. In addition, the aralkyl group may be optionally substituted. Examples of aralkyl groups include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl tert-butyl, α-naphthylmethyl, 1-α-naphthyl-ethyl, 2-α-naphthylethyl, 1-α-naphthylisopropyl, 2-α-naphthylisopropyl, β-naphthylmethyl, 1-β-naphthyl-ethyl, 2-β-naphthyl-ethyl, 1-β-naphthylisopropyl, 2-β-naphthylisopropyl, p-methylbenzyl, m-methylbenzyl, Preferably, benzyl, p-chlorobenzyl, m-chlorobenzyl, o-chlorobenzyl, p-bromobenzyl, m-bromobenzyl, o-bromobenzyl, p-iodobenzyl, m-iodobenzyl, o-iodobenzyl, p-hydroxybenzyl, m-hydroxybenzyl, o-hydroxybenzyl, p-aminobenzyl, m-aminobenzyl, o-aminobenzyl, p-nitrobenzyl, m-nitrobenzyl, o-nitrobenzyl, p-cyanobenzyl, m-cyanobenzyl, o-cyanobenzyl, 1-hydroxy-2-phenylisopropyl and 1-chloro-2-phenylisopropyl are used. Among the above, benzyl, p-cyanobenzyl, m-cyanobenzyl, o-cyanobenzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl and 2-phenylisopropyl are preferred.

[0064] The term "aza" in azadibenzofuran, aza-dibenzothiophene, etc. means that one or more CH groups in the corresponding aromatic fragment are replaced by a nitrogen atom. For example, azatriphenylene includes dibenzo[f,h]quinoxaline, dibenzo[f,h]quinoline and other analogs having two or more nitrogens in the ring system. Other nitrogen analogs of the above-mentioned aza derivatives can be easily thought of by those of ordinary skill in the art, and all such analogs are determined to be included in the terms described herein.

[0065] In the present disclosure, unless otherwise defined, when any one of the terms in the group consisting of substituted alkyl, substituted cycloalkyl, substituted heteroalkyl, substituted aralkyl, substituted alkoxy, substituted aryloxy, substituted alkenyl, substituted aryl, substituted heteroaryl, substituted alkylsilyl, substituted arylsilyl, substituted amine, substituted acyl, substituted carbonyl, substituted carboxylic acid, substituted ester, substituted sulfinyl, substituted sulfonyl, substituted phosphino is used, it means that any one of alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, aryloxy, alkenyl, aryl, heteroaryl, alkylsilyl, arylsilyl, amine, acyl, carbonyl, carboxylic acid, ester, sulfinyl, sulfonyl and phosphino may be substituted by one or more selected from deuterium, halogen, unsubstituted 1-H- 2- 1 ... -20 carbon atoms, alkyl, unsubstituted cycloalkyl, unsubstituted heteroalkyl, unsubstituted arylalkyl, unsubstituted aryloxy, unsubstituted alkenyl, unsubstituted aryl, unsubstituted heteroaryl, unsubstituted alkylsilyl, unsubstituted alkylsilyl, unsubstituted arylsilyl, unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof.

[0066] It should be understood that when describing a molecular fragment as a substituent or otherwise attached to another moiety, its name can be written according to whether it is a fragment (e.g., phenyl, phenylene, naphthyl, dibenzofuranyl) or according to whether it is a whole molecule (e.g., benzene, naphthalene, dibenzofuran). As used herein, these different ways of specifying a substituent or attaching a fragment are considered equivalent.

[0067] In the compounds mentioned in this disclosure, hydrogen atoms may be partially or completely replaced by deuterium. Other atoms such as carbon and nitrogen may also be replaced by their other stable isotopes. The replacement of other stable isotopes in the compounds may be preferred because it enhances the efficiency and stability of the device.

[0068] In the compounds mentioned in the present disclosure, multiple substitution refers to the range including disubstitution up to the maximum number of available substitutions. When a substituent in the compounds mentioned in the present disclosure represents multiple substitutions (including disubstitution, trisubstitution, tetrasubstitution, etc.), it means that the substituent can exist in multiple available substitution positions on its connection structure, and the substituents existing in multiple available substitution positions can be of the same structure or different structures.

[0069] In the compounds mentioned in the present disclosure, unless explicitly defined, for example, adjacent substituents can be optionally connected to form a ring, otherwise adjacent substituents in the compound cannot be connected to form a ring. In the compounds mentioned in the present disclosure, adjacent substituents can be optionally connected to form a ring, including both the situation where adjacent substituents can be connected to form a ring and the situation where adjacent substituents are not connected to form a ring. When adjacent substituents can be optionally connected to form a ring, the formed ring can be a monocyclic or polycyclic ring, as well as an alicyclic, heteroalicyclic, aromatic or heteroaromatic ring. In this statement, adjacent substituents can refer to substituents bonded to the same atom, substituents bonded to carbon atoms directly bonded to each other, or substituents bonded to carbon atoms further away. Preferably, adjacent substituents refer to substituents bonded to the same carbon atom and substituents bonded to carbon atoms directly bonded to each other.

[0070] The expression that adjacent substituents can be optionally linked to form a ring is also intended to be taken to mean that two substituents bonded to the same carbon atom are linked to each other by a chemical bond to form a ring, which can be exemplified by the following formula:

[0071]

[0072] The expression that adjacent substituents can be optionally linked to form a ring is also intended to be taken to mean that two substituents bonded to carbon atoms directly bonded to each other are linked to each other by a chemical bond to form a ring, which can be exemplified by the following formula:

[0073]

[0074] Furthermore, the statement that adjacent substituents can be optionally linked to form a ring is also intended to be taken to mean that, in the case where one of the two substituents bonded to the carbon atoms directly bonded to each other represents hydrogen, the second substituent is bonded at the position to which the hydrogen atom is bonded, thereby forming a ring. This is exemplified by the following formula:

[0075]

[0076] According to one embodiment of the present invention, a metal complex is disclosed, which comprises a ligand L a , L a Having a structure represented by Formula 1:

[0077]

[0078] Wherein, Ring A and Ring B are each independently selected from a five-membered unsaturated carbocyclic ring, an aromatic ring having 6 to 30 carbon atoms, or a heteroaromatic ring having 3 to 30 carbon atoms;

[0079] R i Each occurrence of R is the same or different, indicating mono-, poly- or unsubstituted; iiEach occurrence is identical or different and indicates mono-, poly-, or unsubstituted;

[0080] Y is selected from SiR y R y ,GeR y R y , NR y , P.R. y , O, S or Se;

[0081] When there are two R y When two R y can be the same or different; for example, when Y is selected from SiR y R y When two R y can be the same or different; for example, when Y is selected from GeR y R y When two R y Can be the same or different;

[0082] X1-X2 are selected from CR in the same or different ways each time they appear x or N;

[0083] R, R i , R ii , R x and R y The alkyl radicals are selected, at each occurrence, identically or differently, from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl radicals having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl radicals having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl radicals having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl radicals having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy radicals having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy radicals having 6 to 30 carbon atoms, substituted or unsubstituted substituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amine groups, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;

[0084] Adjacent substituent R i , R x , R y , R and R ii can optionally be linked to form a ring;

[0085] The metal is selected from metals having a relative atomic mass greater than 40.

[0086] In this context, adjacent substituents R i , R x , R y , R and R ii can be optionally linked to form a ring, which is intended to represent adjacent substituent groups, for example, two substituents R i Between the two substituents R ii Between the two substituents R y Between the two substituents R x Between, the substituent R i With R x Between the substituents R and R y Between, and the substituent R ii Any one or more of these substituent groups may be connected to form a ring between R. Obviously, none of these substituents may be connected to form a ring.

[0087] According to one embodiment of the present invention, the metal complex optionally comprises other ligands, which may be combined with the L a Optionally linked to form a tridentate, tetradentate, pentadentate or hexadentate ligand.

[0088] According to one embodiment of the present invention, ring A and ring B are each independently selected from a five-membered unsaturated carbocyclic ring, an aromatic ring having 6 to 18 carbon atoms, or a heteroaromatic ring having 3 to 18 carbon atoms.

[0089] According to one embodiment of the present invention, ring A or ring B is each independently selected from a five-membered unsaturated carbocyclic ring, an aromatic ring having 6 to 18 carbon atoms, or a heteroaromatic ring having 3 to 18 carbon atoms.

[0090] According to one embodiment of the present invention, ring A and ring B are each independently selected from a five-membered unsaturated carbocyclic ring, an aromatic ring having 6 to 10 carbon atoms, or a heteroaromatic ring having 3 to 10 carbon atoms.

[0091] According to one embodiment of the present invention, ring A or ring B is each independently selected from a five-membered unsaturated carbocyclic ring, an aromatic ring having 6-10 carbon atoms, or a heteroaromatic ring having 3-10 carbon atoms.

[0092] According to one embodiment of the present invention, wherein said L a A structure selected from any one of Formula 2 to Formula 19 and Formula 22-Formula 23:

[0093]

[0094]

[0095] in,

[0096] In Formula 2-19 and Formula 22-23, X1-X2 are each independently selected from CR x or N; X3-X7 are each independently selected from CR i or N; A1-A6 are each independently selected from CR ii or N;

[0097] Each occurrence of Z is selected from CR iii R iii ,SiR iii R iii , P.R. iii , O, S or NR iii ; When there are two R iii When two R iii same or different; for example, when Z is selected from CR iii R iii When two R iii same or different; for example, when Z is selected from SiR iii R iii When two R iii Same or different;

[0098] Y is selected from SiR y R y , NR y , P.R. y , O, S or Se; when there are two R y When two R y can be the same or different; for example, when Y is selected from SiR y R y When two R y Can be the same or different;

[0099] R, R i , R ii , R x , R iiiThe alkyl radicals are selected, at each occurrence, identically or differently, from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl radicals having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl radicals having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl radicals having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl radicals having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy radicals having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy radicals having 6 to 30 carbon atoms, substituted or unsubstituted substituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amine groups, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;

[0100] Adjacent substituents R, R x , R y , R i , R ii , R iii Can optionally be linked to form a ring.

[0101] In this context, adjacent substituents R, R x , R y , R i , R ii , R iii can be optionally linked to form a ring, which is intended to represent adjacent substituent groups, for example, two substituents R i Between the two substituents R ii Between the two substituents R x Between the two substituents R y Between the two substituents R iii Between, the substituent R i With R x Between, the substituent R ii With R iii Between the substituents R and R y Between, the substituent R y With R iii between the substituents R and R iii Any one or more of these substituent groups may be connected to form a ring. Obviously, none of these substituent groups may be connected to form a ring.

[0102] According to one embodiment of the present invention, L a A structure selected from Formula 2, Formula 9, Formula 11 or Formula 12.

[0103] According to one embodiment of the present invention, L a A structure represented by Formula 2 is selected.

[0104] According to one embodiment of the present invention, in Formula 2-Formula 19 and Formula 22-Formula 23, X1-X n and / or A1-A m At least one of the X is selected from N, n Corresponding to the largest sequence number of X1-X7 in any one of Formula 2-Formula 19 and Formula 22-Formula 23, the A m The corresponding A1-A6 in any one of Formula 2-Formula 19 and Formula 22-Formula 23 has the largest sequence number; for example, for Formula 2, the X n Corresponding to the largest number X5 of X1-X7 in Formula 2, the A m The largest number A4 of A1-A6 in Formula 2 corresponds to A4, that is, in Formula 2, at least one of X1-X5 and / or A1-A4 is selected from N. For another example, for Formula 12, X n Corresponding to the largest number X3 of X1-X7 in formula 12, the A m The largest serial number A4 corresponding to A1-A6 in Formula 12, that is, at least one of X1-X3 and / or A1-A4 in Formula 12 is selected from N.

[0105] According to one embodiment of the present invention, in Formula 2-Formula 19 and Formula 22-Formula 23, X1-X n At least one of the X is selected from N, n The corresponding X1-X7 has the largest serial number in any one of Formula 2-Formula 19 and Formula 22-Formula 23.

[0106] According to one embodiment of the present invention, in Formula 2-Formula 19 and Formula 22-Formula 23, X2 is N.

[0107] According to one embodiment of the present invention, in Formula 2-Formula 19 and Formula 22-Formula 23, X1-X2 are each independently selected from CR x ; X3-X7 are each independently selected from CR i ; A1-A6 are each independently selected from CR ii ; Adjacent substituent R x , R i , R ii Can optionally be linked to form a ring.

[0108] In this embodiment, the adjacent substituent R x , R i , R iican be optionally linked to form a ring, which is intended to represent adjacent substituent groups, for example, two substituents R i Between the two substituents R ii Between the two substituents R x Between, and the substituent R i With R x Any one or more of these substituent groups may be connected to form a ring. Obviously, none of these substituent groups may be connected to form a ring.

[0109] According to one embodiment of the present invention, in Formula 2-Formula 19 and Formula 22-Formula 23, X1-X2 are each independently selected from CR x ; X3-X7 are each independently selected from CR i ; A1-A6 are each independently selected from CR ii ; and said R x , R i , R ii each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, cyano, and combinations thereof; the adjacent substituent R x , R i , R ii Can optionally be linked to form a ring.

[0110] According to one embodiment of the present invention, in Formula 2-Formula 19 and Formula 22-Formula 23, X1-X2 are each independently selected from CR x ; X3-X7 are each independently selected from CR i ; A1-A6 are each independently selected from CR ii ; and said R x , R i , R ii At least two of the substituents R are selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, cyano, and combinations thereof; the adjacent substituent R x , R i , Rii Can optionally be linked to form a ring.

[0111] In this embodiment, the R x , R i , R ii At least two of them are selected from the group of substituents, the same or different, at each occurrence, and are intended to represent a substituent group consisting of two R x Substituents, all R i Substituents and all R ii In a group of substituents, at least two substituents are selected from the group of substituents, the same or different, on each occurrence.

[0112] According to one embodiment of the present invention, in Formula 2-Formula 19 and Formula 22-Formula 23, X1-X2 are each independently selected from CR x ; X3-X7 are each independently selected from CR i ; A1-A6 are each independently selected from CR ii ; and said R x , R i , R ii At least three of the following are selected from the group consisting of deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, cyano, and combinations thereof; the adjacent substituent R x , R i , R ii Can optionally be linked to form a ring.

[0113] In this embodiment, the R x , R i , R ii At least three of them are selected from the group of substituents, the same or different, at each occurrence, to indicate that in the case of two R x Substituents, all R i Substituents and all R ii At least three substituents in the group of substituents are selected from the group of substituents identically or differently on each occurrence.

[0114] According to one embodiment of the present invention, in Formula 2-Formula 11 and Formula 22-Formula 23, X4 and X5 are each independently selected from CR i In formula 12-19, X3 is selected from CR i .

[0115] According to one embodiment of the present invention, in Formula 2-Formula 11 and Formula 22-Formula 23, X4 or X5 is selected from CR i In formula 12-19, X3 is selected from CR i .

[0116] According to one embodiment of the present invention, in Formula 2-Formula 11 and Formula 22-Formula 23, X4 and X5 are each independently selected from CR i In formula 12-19, X3 is selected from CR i ; and said R i Each occurrence is identically or differently selected from hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilanyl having 6 to 20 carbon atoms, cyano, or a combination thereof.

[0117] According to one embodiment of the present invention, in Formula 2-Formula 11 and Formula 22-Formula 23, X4 or X5 is selected from CR i In formula 12-19, X3 is selected from CR i ; and said R i Each occurrence is identically or differently selected from hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilanyl having 6 to 20 carbon atoms, cyano, or a combination thereof.

[0118] According to one embodiment of the present invention, in Formula 2-Formula 11 and Formula 22-Formula 23, X4 and X5 are each independently selected from CR i In formula 12-19, X3 is selected from CR i ; wherein said R i Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, fluorine, methyl, ethyl, isopropyl, isobutyl, tert-butyl, neopentyl, cyclopentyl, cyclopentylmethyl, cyclohexyl, norbornyl, adamantyl, trimethylsilyl, isopropyldimethylsilyl, phenyldimethylsilyl, trifluoromethyl, cyano, phenyl, and combinations thereof.

[0119] According to one embodiment of the present invention, in Formula 2-Formula 11 and Formula 22-Formula 23, X4 or X5 is selected from CR iIn formula 12-19, X3 is selected from CR i ; wherein said R i Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, fluorine, methyl, ethyl, isopropyl, isobutyl, tert-butyl, neopentyl, cyclopentyl, cyclopentylmethyl, cyclohexyl, norbornyl, adamantyl, trimethylsilyl, isopropyldimethylsilyl, phenyldimethylsilyl, trifluoromethyl, cyano, phenyl, and combinations thereof.

[0120] According to one embodiment of the present invention, in Formula 2-Formula 19 and Formula 22-Formula 23, R is selected from hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, or a combination thereof.

[0121] According to one embodiment of the present invention, in Formula 2-Formula 19 and Formula 22-Formula 23, R is selected from hydrogen, deuterium, fluorine, methyl, ethyl, isopropyl, isobutyl, tert-butyl, neopentyl, cyclopentyl, cyclopentylmethyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated tert-butyl, deuterated neopentyl, deuterated cyclopentyl, deuterated cyclopentylmethyl, deuterated cyclohexyl, trimethylsilyl, or a combination thereof.

[0122] According to one embodiment of the present invention, in Formula 2-Formula 19 and Formula 22-Formula 23, Y is selected from O or S.

[0123] According to one embodiment of the present invention, in Formula 2-Formula 19 and Formula 22-Formula 23, Y is selected from O.

[0124] According to one embodiment of the present invention, in Formula 2-Formula 19 and Formula 22-Formula 23, X1 and X2 are each independently selected from CR x .

[0125] According to one embodiment of the present invention, in Formula 2-Formula 19 and Formula 22-Formula 23, X1 and X2 are each independently selected from CR x ; and said R xEach occurrence is identically or differently selected from hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, or a combination thereof.

[0126] According to one embodiment of the present invention, in Formula 2-Formula 19 and Formula 22-Formula 23, X1 is selected from CR x , X2 is N.

[0127] According to one embodiment of the present invention, in Formula 2-Formula 19 and Formula 22-Formula 23, X1 is selected from CR x , X2 is N; and said R x Each occurrence is identically or differently selected from hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, or a combination thereof.

[0128] According to one embodiment of the present invention, the ligand L a Having a structure represented by Formula 20 or Formula 21:

[0129]

[0130] Among them, in equation 20 and equation 21,

[0131] Y is selected from O or S;

[0132] R x1 , R x2 , R i1 , R i2 , R i3 , R ii1 , R ii2 , R ii3 , R ii4each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, or a combination thereof;

[0133] R is selected, at each occurrence, identically or differently, from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted amine having 0-20 carbon atoms, and combinations thereof.

[0134] According to one embodiment of the present invention, the ligand L a Having a structure represented by Formula 20 or Formula 21:

[0135]

[0136] Among them, in equation 20 and equation 21,

[0137] Y is selected from O or S;

[0138] R x1 , R x2 , R i1 , R i2 , R i3 Neutralize and / or R ii1 , R ii2 , R ii3 , R ii4At least one or two of the above are selected, at each occurrence, identically or differently, from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 6 to 20 carbon atoms R is selected from halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, or a combination thereof.

[0139] According to one embodiment of the present invention, the ligand L a Having a structure represented by Formula 20 or Formula 21:

[0140]

[0141] Among them, in equation 20 and equation 21,

[0142] Y is selected from O or S;

[0143] R x1 , R x2 , R i1 , R i2 , R i3 Neutralize and / or R ii1 , R ii2 , R ii3 and R ii4 At least one or two of them are selected from the group consisting of: substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, or a combination thereof; R is selected from substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, or a combination thereof.

[0144] According to one embodiment of the present invention, the ligand L a Having a structure represented by Formula 20 or Formula 21:

[0145]

[0146] Among them, in equation 20 and equation 21,

[0147] Y is selected from O or S;

[0148] R i2 Selected from the group consisting of deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, or a combination thereof;

[0149] R is selected from the group consisting of halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, or a combination thereof; R ii1 , R ii2 , R ii3 , R ii4 At least one or two of the above are selected, at each occurrence, identically or differently, from the group consisting of deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, or a combination thereof.

[0150] According to one embodiment of the present invention, the ligand L a Having a structure represented by Formula 20 or Formula 21:

[0151]

[0152] Among them, in equation 20 and equation 21,

[0153] Y is selected from O or S;

[0154] R i2Selected from the group consisting of: a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, or a combination thereof;

[0155] R is selected from the group consisting of a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, or a combination thereof; R ii1 , R ii2 , R ii3 , R ii4 At least one or two of the above are selected, at each occurrence, identically or differently, from the group consisting of a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, or a combination thereof.

[0156] According to one embodiment of the present invention, in Formula 20 and Formula 21, R ii1 , R ii2 , R ii3 One of the ii1 or R ii2 or R ii3 ) or two (for example, R ii1 and R ii2 , or R ii2 and R ii3 , or R ii1 and R ii3 ) is selected, at each occurrence, identically or differently, from the group consisting of substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, or a combination thereof.

[0157] According to one embodiment of the present invention, in Formula 20 and Formula 21, R x1 , R x2 , R i1 , R i2 , R i3 , R ii1 , R ii2 , R ii3 , R ii4 , at least one of R is selected, at each occurrence, identically or differently, from the group consisting of: substituted or unsubstituted alkyl having 3-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, and combinations thereof.

[0158] In this embodiment, R x1 , R x2 , R i1 , R i2 , R i3 , R ii1 , R ii2 , R ii3 , R ii4 , at least one of R is selected from the group of substituents the same or different each time it occurs, and is intended to represent: R x1 , R x2 At least one of each occurrence is selected from the group of substituents identically or differently, and / or R i1 , R i2 , R i3 At least one of each occurrence is selected from the group of substituents identically or differently, and / or R ii1 , R ii2 , R ii3 , R ii4 At least one of each occurrence is selected identically or differently from said substituent group, and / or R is selected from said substituent group.

[0159] According to one embodiment of the present invention, in Formula 20 and Formula 21, R i2 , R i3 , R ii1 , R ii2 , R ii3 , at least one of R is selected, at each occurrence, identically or differently, from the group consisting of: substituted or unsubstituted alkyl having 3-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, and combinations thereof.

[0160] In this embodiment, R i2 , R i3 , R ii1 , Rii2 , R ii3 , at least one of R is selected from the group of substituents the same or different each time it occurs, and is intended to represent: R i2 , R i3 At least one of each occurrence is selected from the group of substituents identically or differently, and / or R ii1 , R ii2 , R ii3 At least one of each occurrence is selected identically or differently from said substituent group, and / or R is selected from said substituent group.

[0161] According to one embodiment of the present invention, in Formula 20 and Formula 21, R x1 , R x2 , R i1 , R i2 , R i3 , R ii1 , R ii2 , R ii3 , R ii4 , at least one of R is selected, at each occurrence, identically or differently, from the group consisting of substituted or unsubstituted alkyl having 3 to 10 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 10 ring carbon atoms, and combinations thereof.

[0162] In this embodiment, R x1 , R x2 , R i1 , R i2 , R i3 , R ii1 , R ii2 , R ii3 , R ii4 , at least one of R is selected from the group of substituents the same or different each time it occurs, and is intended to represent: R x1 , R x2 At least one of each occurrence is selected from the group of substituents identically or differently, and / or R i1 , R i2 , R i3 At least one of each occurrence is selected from the group of substituents identically or differently, and / or R ii1 , R ii2 , R ii3 , R ii4 At least one of each occurrence is selected identically or differently from said substituent group, and / or R is selected from said substituent group.

[0163] According to one embodiment of the present invention, L a Each time it appears, choose the same or different one from L a1 To L a1706 The group composed of.

[0164] According to one embodiment of the present invention, L a Each time it appears, choose the same or different one from L a1 To L a1803 The group composed of.

[0165] According to one embodiment of the present invention, L a Each time it appears, choose the same or different one from L a1 To L a1931 A group consisting of, wherein the L a1 To L a1931 The specific structure is:

[0166]

[0167]

[0168]

[0169]

[0170]

[0171]

[0172]

[0173]

[0174]

[0175]

[0176]

[0177]

[0178]

[0179]

[0180]

[0181]

[0182]

[0183]

[0184]

[0185]

[0186]

[0187]

[0188]

[0189]

[0190]

[0191]

[0192]

[0193]

[0194]

[0195]

[0196]

[0197]

[0198]

[0199]

[0200]

[0201]

[0202]

[0203]

[0204]

[0205]

[0206]

[0207]

[0208]

[0209]

[0210]

[0211]

[0212]

[0213]

[0214]

[0215]

[0216]

[0217]

[0218]

[0219]

[0220]

[0221]

[0222]

[0223] In the above structure, TMS is trimethylsilyl.

[0224] According to one embodiment of the present invention, wherein the L a1 To L a1931 The hydrogen in the structure can be partially or completely replaced by deuterium.

[0225] According to one embodiment of the present invention, the metal complex has M(L a ) m (L b ) n (L c ) q structure;

[0226] Wherein, the metal M is selected from metals with a relative atomic mass greater than 40; L a , L b and L c are the first ligand, the second ligand and the third ligand of the complex respectively; m is 1, 2 or 3, n is 0, 1 or 2, q is 0, 1 or 2, m+n+q is equal to the oxidation state of the metal M; when m is greater than 1, multiple L a The same or different; when n is 2, the two L b The same or different; when q is 2, the two L c Same or different;

[0227] L a , L b and L c can optionally be linked to form a multidentate ligand; for example, L a , L b and L c Can be optionally linked to form a tetradentate ligand or a hexadentate ligand; L a , L b and L c It is also possible that none of them are connected so as not to form a multidentate ligand;

[0228] L b and L c Each occurrence is identically or differently selected from the group consisting of:

[0229]

[0230] Among them, R a , R b and R c Each occurrence is identical or different and indicates mono-, poly-, or unsubstituted;

[0231] X b Each occurrence is identically or differently selected from the group consisting of: O, S, Se, NR N1 and CR C1 R C2 ;

[0232] X c and X d Each occurrence is identically or differently selected from the group consisting of: O, S, Se and NR N2 ;

[0233] R a , R b , R c , R N1 , R N2 , R C1 and R C2Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted substituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amine groups, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;

[0234] Among them, the adjacent substituent R a , R b , R c , R N1 , R N2 , R C1 and R C2 Can optionally be linked to form a ring.

[0235] In this embodiment, the adjacent substituent R a , R b , R c , R N1 , R N2 , R C1 and R C2 can be optionally linked to form a ring, which is intended to represent adjacent substituent groups, for example, two substituents R a Between the two substituents R b Between the two substituents R c Between, the substituent R a and R b Between, the substituent R a and R c Between, the substituent R b and R c Between, the substituent R a and R N1 Between, the substituent R b and R N1 Between, the substituent R a and R C1 Between, the substituent R a and R C2 Between, the substituent R b and R C1 Between, the substituent Rb and R C2 Between, the substituent R a and R N2 Between, the substituent R b and R N2 Between, and R C1 and R C2 Any one or more of these substituent groups may be connected to form a ring. Obviously, none of these substituent groups may be connected to form a ring.

[0236] In this embodiment, L a , L b and L c can be optionally linked to form a multidentate ligand, and is intended to represent L a , L b and L c Any two or three of L can be linked to form a tetradentate ligand or a hexadentate ligand. a , L b and L c It is also possible that none of them are connected so as not to form a multidentate ligand.

[0237] According to one embodiment of the present invention, the metal M is selected from Ir, Rh, Re, Os, Pt, Au or Cu.

[0238] According to one embodiment of the present invention, the metal M is selected from Ir, Pt or Os.

[0239] According to an embodiment of the present invention, the metal M is Ir.

[0240] According to one embodiment of the present invention, L b Each occurrence is identically or differently selected from the following structures:

[0241]

[0242] wherein R1-R7 are selected, at each occurrence, identically or differently, from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amine groups, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups having 0 to 20 carbon atoms, and combinations thereof.

[0243] According to one embodiment of the present invention, L b Each occurrence is identically or differently selected from the following structures:

[0244]

[0245] wherein at least one of R1-R3 is selected from substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, or a combination thereof; and / or at least one of R4-R6 is substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, or a combination thereof.

[0246] According to one embodiment of the present invention, L b Each occurrence is identically or differently selected from the following structures:

[0247]

[0248] wherein at least two of R1-R3 are selected from substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, or a combination thereof; and / or at least one of R4-R6 is substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, or a combination thereof.

[0249] According to one embodiment of the present invention, Lb Each occurrence is identically or differently selected from the following structures:

[0250]

[0251] wherein at least two of R1-R3 are selected from substituted or unsubstituted alkyl groups having 2-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 2-20 carbon atoms, or a combination thereof; and / or at least two of R4-R6 are selected from substituted or unsubstituted alkyl groups having 2-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 2-20 carbon atoms, or a combination thereof.

[0252] According to one embodiment of the present invention, L b Each time it appears, choose the same or different one from L b1 To L b322 Groups composed of:

[0253]

[0254]

[0255]

[0256]

[0257]

[0258]

[0259]

[0260] L c Each time it appears, choose the same or different one from L c1 To L c231 Groups composed of:

[0261]

[0262]

[0263]

[0264]

[0265]

[0266]

[0267] According to one embodiment of the present invention, the metal complex has Ir(L a )2(L b ) or Ir(L a )2(L c ) or Ir(L a )(L c )2 structure;

[0268] Wherein, when the metal complex has Ir(L a )2(L b ) structure, L a Each time it appears, choose the same or different one from L a1 To L a1706 Any one or two of the group consisting of L b Choose from L b1 To L b322 When the metal complex has Ir(L a )2(L c ) structure, L a Each time it appears, choose the same or different one from L a1 To L a1706 Any one or two of the group consisting of L c Choose from L c1 To L c231 When the metal complex has Ir(L a )(L c )2 structure, L a Choose from L a1 To L a1706 Any of the groups consisting of L c Each time it appears, choose the same or different one from L c1 -L c231 Any one or any two of the group consisting of.

[0269] According to one embodiment of the present invention, the metal complex has Ir(L a )2(L b ) or Ir(L a )2(L c ) or Ir(L a )(L c )2 structure;

[0270] Wherein, when the metal complex has Ir(L a )2(L b ) structure, L a Each time it appears, choose the same or different one from L a1 To L a1803Any one or two of the group consisting of L b Choose from L b1 To L b322 When the metal complex has Ir(L a )2(L c ) structure, L a Each time it appears, choose the same or different one from L a1 To L a1803 Any one or two of the group consisting of L c Choose from L c1 To L c231 When the metal complex has Ir(L a )(L c )2 structure, L a Choose from L a1 To L a1803 Any of the groups consisting of L c Each time it appears, choose the same or different one from L c1 -L c231 Any one or any two of the group consisting of.

[0271] According to one embodiment of the present invention, the metal complex has Ir(L a )2(L b ) or Ir(L a )2(L c ) or Ir(L a )(L c )2 structure;

[0272] Wherein, when the metal complex has Ir(L a )2(L b ) structure, L a Each time it appears, choose the same or different one from L a1 To L a1931 Any one or two of the group consisting of L b Choose from L b1 To L b322 When the metal complex has Ir(L a )2(L c ) structure, L a Each time it appears, choose the same or different one from L a1 To L a1931 Any one or two of the group consisting of L c Choose from L c1 To L c231 When the metal complex has Ir(L a )(Lc )2 structure, L a Choose from L a1 To L a1931 Any of the groups consisting of L c Each time it appears, choose the same or different one from L c1 -L c231 Any one or any two of the group consisting of.

[0273] According to one embodiment of the present invention, the metal complex is selected from the group consisting of Compound 1 to Compound 260.

[0274] According to one embodiment of the present invention, the metal complex is selected from the group consisting of Compound 1 to Compound 290.

[0275] According to one embodiment of the present invention, the metal complex is selected from the group consisting of Compound 1 to Compound 312;

[0276] wherein compounds 1 to 200 and compounds 261 to 312 have Ir(L a )2(L b ) structure, where two L a Same, L a and L b The corresponding structures are selected from the following table:

[0277]

[0278]

[0279]

[0280] Among them, compounds 201 to 260 have Ir(L a )2(L b ) structure, where two L a Different, L a and L b The corresponding structures are selected from the following table:

[0281]

[0282] According to one embodiment of the present invention, an electroluminescent device is also disclosed, comprising:

[0283] anode,

[0284] cathode,

[0285] and an organic layer disposed between the anode and the cathode, the organic layer comprising a metal complex comprising a ligand La , L a Having a structure represented by Formula 1:

[0286]

[0287] Wherein, Ring A and Ring B are each independently selected from a five-membered unsaturated carbocyclic ring, an aromatic ring having 6 to 30 carbon atoms, or a heteroaromatic ring having 3 to 30 carbon atoms;

[0288] R i Each occurrence of R is the same or different, indicating mono-, poly- or unsubstituted; ii Each occurrence is identical or different and indicates mono-, poly-, or unsubstituted;

[0289] Y is selected from SiR y R y ,GeR y R y , NR y , P.R. y , O, S or Se;

[0290] When there are two R y When two R y Can be the same or different;

[0291] X1-X2 are selected from CR in the same or different ways each time they appear x or N;

[0292] R, R i , R ii , R x and R y Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted an alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amine group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;

[0293] Adjacent substituent R i , Rx , R y , R and R ii can optionally be linked to form a ring;

[0294] The metal is selected from metals having a relative atomic mass greater than 40.

[0295] According to an embodiment of the present invention, in the electroluminescent device, the organic layer is a light-emitting layer, and the metal complex is a light-emitting material.

[0296] According to an embodiment of the present invention, the electroluminescent device emits red light.

[0297] According to an embodiment of the present invention, the electroluminescent device emits white light.

[0298] According to an embodiment of the present invention, in the electroluminescent device, the organic layer is a light-emitting layer, and the light-emitting layer further comprises at least one host material.

[0299] According to one embodiment of the present invention, in the electroluminescent device, the at least one host material contains at least one chemical group selected from the group consisting of: benzene, pyridine, pyrimidine, triazine, carbazole, azacarbazole, indolecarbazole, dibenzothiophene, azadibenzothiophene, dibenzofuran, azadibenzofuran, dibenzoselenophene, triphenylene, azatriphenylene, fluorene, silylfluorene, naphthalene, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene, azaphenanthrene, and combinations thereof.

[0300] According to another embodiment of the present invention, a compound combination is also disclosed, which includes a metal complex, and the specific structure of the metal complex is shown in any of the above embodiments.

[0301] Combination with other materials

[0302] The materials for specific layers in the organic light-emitting device described in the present invention can be used in combination with various other materials present in the device. The combination of these materials is described in detail in paragraphs 0132-0161 of U.S. Patent Application US2016 / 0359122A1, the entire contents of which are incorporated herein by reference. The materials described or mentioned therein are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and those skilled in the art can easily consult the literature to identify other materials that can be used in combination.

[0303] The materials described herein as specific layers that can be used in organic light-emitting devices can be used in combination with a variety of other materials present in the device. For example, the light-emitting dopants disclosed herein can be used in combination with a variety of hosts, transport layers, barrier layers, injection layers, electrodes, and other layers that may be present. The combination of these materials is described in detail in paragraphs 0080-0101 of U.S. Patent Application US2015 / 0349273A1, the entire contents of which are incorporated herein by reference. The materials described or mentioned therein are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and those skilled in the art can easily consult the literature to identify other materials that can be used in combination.

[0304] In the embodiment of material synthesis, unless otherwise stated, all reactions are carried out under nitrogen protection. All reaction solvents are anhydrous and used as they are from commercial sources. The synthetic product uses one or more conventional equipment in the art (including but not limited to Bruker's nuclear magnetic resonance instrument, Shimadzu's liquid chromatograph, liquid chromatography-mass spectrometer, gas chromatography-mass spectrometer, differential scanning calorimeter, Shanghai Lingguang Technology's fluorescence spectrophotometer, Wuhan Cost's electrochemical workstation, Anhui Bei Yi Ke's sublimator, etc.), and the structure is confirmed and the characteristics are tested by methods well known to those skilled in the art. In the embodiment of the device, the characteristics of the device are also tested by methods well known to those skilled in the art using conventional equipment in the art (including but not limited to Angstrom Engineering's evaporation machine, Suzhou Fushida's optical test system, life test system, Beijing Liangtuo's ellipsometer, etc.). Since those skilled in the art are aware of the use of the above-mentioned equipment, test methods and other related contents, it is possible to obtain the inherent data of the sample with certainty and without being affected, so the above-mentioned related contents are no longer expanded in this patent.

[0305] Material synthesis example:

[0306] The preparation method of the compound of the present invention is not limited, and the following compounds are typically but not limitedly exemplified, and their synthetic routes and preparation methods are as follows:

[0307] Synthesis Example 1: Synthesis of Compound 81

[0308] Step 1: Synthesis of intermediate 2

[0309]

[0310] 5 g of raw material 1 (24.03 mmol) was dissolved in 50 mL of DCM, and 5.39 g (1.3 eq, 31.24 mmol) of m-CPBA (meta-chloroperbenzoic acid) was added at room temperature. The mixture was stirred for 24 h. TLC showed that the raw material disappeared. The solvent was removed in vacuo, and the obtained crude intermediate 2 was directly used in the next step.

[0311] Step 2: Synthesis of intermediate 3

[0312]

[0313] The intermediate 2 obtained in step 1 was dissolved in 24 mL of phosphorus oxychloride, heated to 100°C, stirred for 3 h, cooled to 0°C, and slowly added with aqueous NaOH solution until pH = 9, extracted with DCM three times (50 mL * 3), the organic phases were combined, washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and the solvent was removed in vacuo. Purification by column chromatography (PE: EA = 30: 1) gave 1.98 g of intermediate 3, with a two-step yield of 34%.

[0314] Step 3: Synthesis of intermediate 5

[0315]

[0316] 3g (18.96mmol) of intermediate 4 was dissolved in 30mL of anhydrous tetrahydrofuran, cooled to -78°C, and n-BuLi (1M, 22.75mL) (1.2eq, 22.75mmol) was slowly added dropwise under nitrogen atmosphere. After the addition was completed, the mixture was warmed to room temperature and stirred for 1h. The mixture was cooled to -78°C, and 4.63g (1.3eq, 24.65mmol) of 1,2-dibromoethane was slowly added dropwise. After the addition was completed, the mixture was warmed to room temperature and stirred overnight. The reaction was quenched with saturated ammonium chloride, extracted three times with EA (40mL*3), the organic phases were combined, washed with saturated sodium chloride aqueous solution, dried with anhydrous magnesium sulfate, and the solvent was removed in vacuo. Purification by column chromatography (PE:EA=100:1) gave 3.82g of intermediate 5 with a yield of 85%.

[0317] Step 4: Synthesis of intermediate 6

[0318]

[0319] 2.5 g of intermediate 5 (10.57 mmol), 0.387 g of PdCl2 (dppf) (0.05 eq, 0.53 mmol), 1.56 g of AcOK (1.5 eq, 15.85 mmol), 3.22 g of B2Pin2 (boronic acid pinacol ester) (1.2 eq, 12.68 mmol) were dissolved in 30 mL of 1,4-dioxane, heated to 80 ° C, and stirred overnight. Cooled to room temperature, the solvent was removed in vacuo, and purified by column chromatography (PE: EA = 20: 1) to obtain 2.21 g of white solid intermediate 6, with a yield of 74%.

[0320] Step 5: Synthesis of intermediate 7

[0321]

[0322] 3.93g of intermediate 6 (1.2eq, 13.85mmol), 2.78g of intermediate 3 (1eq, 11.54mmol), 0.387g of Pd(PPh3)4 (0.05eq, 0.58mmol), 1.83g of Na2CO3 (1.5eq, 17.31mmol) were dissolved in 30mL of 1,4-dioxane and 10mL of water, heated to 90°C, and stirred overnight. Cooled to room temperature, the solvent was removed in vacuo, and purified by column chromatography (PE:EA=50:1) to obtain 3g of white solid intermediate 7, with a yield of 72%.

[0323] Step 6: Synthesis of Intermediate 8

[0324]

[0325] 3.03 g of intermediate 7 (8.32 mmol) was dissolved in 30 mL of DCM, cooled to 0°C, BBr3 was slowly added dropwise under nitrogen atmosphere, stirred for 2 h, the reaction was quenched with aqueous NaHCO3 solution, extracted with DCM (60 mL*3), the organic phases were combined, washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and the solvent was removed in vacuo. Purification by column chromatography (PE:EA=4:1) gave 1.17 g of intermediate 8, with a yield of 40%.

[0326] Step 7: Synthesis of Intermediate 9

[0327]

[0328] 1.2 g of intermediate 8 (1 eq, 3.33 mmol), 24 mg of CuBr (0.05 eq, 0.17 mmol), and 2.82 g of K3PO4 (4 eq, 13.3 mmol) were dissolved in 15 mL of DMF, heated to 90°C, and stirred overnight. The mixture was cooled to room temperature, diluted with water, and the product precipitated. The mixture was filtered through diatomaceous earth and the solid was washed with 1 L of DCM. 0.81 g of intermediate 9 was obtained with a yield of 90%. The obtained yellow solid intermediate 9 was recrystallized from toluene, and the obtained solid intermediate 9 had a purity of 99.7%.

[0329] Step 8: Synthesis of Iridium Dimer

[0330]

[0331] At room temperature, 1.2 g (3 eq, 4.45 mmol) of intermediate 9 was dissolved in 24 mL of 2-ethoxyethanol and 8 mL of water, and 523 mg of IrCl3·3H2O (1 eq, 1.48 mmol) was added. The mixture was ventilated three times at room temperature, heated to 130°C, refluxed at this temperature for 24 hours, and cooled to room temperature. The mixture was filtered, and the solid was washed with ethanol until the washing liquid was colorless. The solid was filtered for about 15 minutes until the ethanol on the solid completely disappeared, and 1.13 g of red solid iridium dimer was obtained with a yield of 99%. The solid was used directly in the next step without purification.

[0332] Step 9: Synthesis of compound 81

[0333]

[0334] 1.13g of iridium dimer (1eq, 0.74mmol) obtained in step 8 was added to a 100mL round-bottom flask, and 510mg of K2CO3 (5eq, 3.7mmol) and 0.74g of 3,7-diethyl-3-methyl-4,6-nonanedione (4eq, 2.96mmol) were added. The mixture was replaced with nitrogen three times at room temperature, stirred for 24 hours under nitrogen protection, filtered with diatomaceous earth, and the solid was washed with ethanol until the washing liquid was colorless. The solid was filtered for about 15 minutes to remove the ethanol adsorbed by the solid. Under vacuum filtration, the red solid on the diatomaceous earth was dissolved in 200mL of dichloromethane, 20mL of ethanol was added to the flask, and the dichloromethane was removed in vacuo. The product was precipitated in the remaining ethanol, filtered, and the ethanol adsorbed by the solid was drained. Purification by silica gel column chromatography (PE: DCM = 10: 1), the obtained crude solid was dissolved in 200 mL of dichloromethane, 20 mL of ethanol was added, dichloromethane was removed in vacuo, the product was precipitated in the remaining ethanol, filtered, and the ethanol adsorbed by the solid was drained to obtain a red solid compound 81 (mass 1.13 g, yield 80%). The purity was 99.6%. The product was confirmed to be the target product with a molecular weight of 954.3.

[0335] Synthesis Example 2: Synthesis of Compound 83

[0336] Step 1: Synthesis of intermediate 11:

[0337]

[0338] The intermediate 10 (7.6 g, 35.1 mmol) was dissolved in 70 mL of ultra-dry tetrahydrofuran, and then the reaction solution was cooled to 0 ° C. Then, n-butyl lithium solution (15.5 mL, 38.7 mmol) was added dropwise under nitrogen protection. After the addition was completed, the temperature was maintained for 1 h. Then, isopropyl alcohol pinacol borate (iPrOBpin, 8.49 g, 45.6 mmol) was added. After the addition was completed, the reaction was heated to room temperature for 2 h, and then a saturated ammonium chloride solution was added to quench the reaction. Then, ethyl acetate was added to the reaction, the liquid was separated, the aqueous phase was extracted with ethyl acetate, the organic phase was combined, dried, and spin-dried to obtain a crude product, which was separated by silica gel column chromatography (eluent: ethyl acetate: petroleum ether = 1:50, v / v) to obtain the target product, colorless oily liquid intermediate 11 (4.7 g, 39.1%).

[0339] Step 2: Synthesis of intermediate 13:

[0340]

[0341] Intermediate 12 (3.19 g, 13.7 mmol), intermediate 11 (4.7 g, 13.7 mmol), tetrakistriphenylphosphine palladium (0.8 g, 0.69 mmol), sodium carbonate (2.18 g, 20.55 mmol), 1,4-dioxane (60 mL) and water (15 mL) were added to a 250 mL round-bottom flask, and then the reaction was heated to 80 ° C under nitrogen protection and stirred overnight. After TLC showed that the reaction was complete, it was cooled to room temperature. Then ethyl acetate was added to the reaction, the liquid was separated, the aqueous phase was extracted with ethyl acetate, the organic phase was combined, dried, and spin-dried to obtain a crude product, which was separated by silica gel column chromatography (eluent ethyl acetate: petroleum ether = 1:10, v / v) to obtain the target product white solid intermediate 13 (3.5 g, 73.0%).

[0342] Step 3: Synthesis of intermediate 14:

[0343]

[0344] Dissolve the intermediate 13 (4.1 g, 10 mmol) in 20 mL of ethanol, then add 20 mL of 2M HCl, heat the reaction to reflux and stir overnight, and cool to room temperature after TLC shows the reaction is complete. Then add saturated sodium carbonate solution to adjust the pH to neutral, and a large amount of yellow solid precipitates in the solution. Filter, wash the solid with water several times, and then drain to obtain the target product, yellow solid intermediate 14 (3.3 g, 93.2%).

[0345] Step 4: Synthesis of intermediate 15:

[0346]

[0347] Intermediate 14 (3.3 g, 9.3 mmol), cuprous bromide (133 mg, 0.9 mmol), 2,2,6,6-tetramethylheptanedione (1.37 g, 7.44 mmol), cesium carbonate (7.6 g, 23.25 mmol) and DMF (90 mL) were heated to 135 ° C under nitrogen protection for overnight reaction, and cooled to room temperature after TLC showed that the reaction was complete. 200 mL of water was added until a large amount of yellow solid precipitated in the solution, filtered, and the solid was washed with water several times and then dried to obtain the target product yellow solid intermediate 15 (3.10 g, 96%).

[0348] Step 5: Synthesis of intermediate 16:

[0349]

[0350] Intermediate 15 (3.42 g, 10.8 mmol), isobutylboric acid (2.2 g, 21.6 mmol), palladium acetate (121 mg, 0.54 mmol), Sphos (443 mg, 1.08 mmol), potassium phosphate trihydrate (8.63 g, 32.4 mmol) and toluene (80 mL) were heated to reflux under nitrogen protection for overnight reaction, and cooled to room temperature after TLC showed that the reaction was complete. It was poured into a funnel filled with diatomaceous earth and filtered, and the filtrate was collected and dried to obtain a crude product, which was separated by silica gel column chromatography (eluent: ethyl acetate: petroleum ether = 1:30, v / v) to obtain the target product yellow solid intermediate 16 (1.8 g, 49.4%).

[0351] Step 6: Synthesis of iridium dimer:

[0352]

[0353] A mixture of intermediate 16 (1.8 g, 5.3 mmol), iridium trichloride trihydrate (628 mg, 1.78 mmol), 2-ethoxyethanol (21 mL) and water (7 mL) was refluxed under nitrogen atmosphere for 24 hours. After cooling to room temperature, the water in the solution was carefully removed on a rotary evaporator to obtain an ethoxyethanol solution of the dimer, which was used in the next step without further purification.

[0354] Step 7: Synthesis of compound 83

[0355]

[0356] The solution of iridium dimer, 3.7-diethyl-3-methylnonane-4,6-dione (663 mg, 2.67 mmol) and potassium carbonate (1.23 g, 8.9 mmol) were added to a 100 mL round-bottom flask and reacted at 60 ° C for 24 hours under nitrogen protection. It was then poured into a funnel filled with diatomaceous earth, filtered and washed with ethanol. Dichloromethane was added to the obtained solid and the filtrate was collected. Ethanol was then added and the obtained solution was concentrated, but not concentrated to dryness. After filtration, 1.1 g of product compound 83 was obtained with a yield of 57%. The product was further purified by column chromatography. The structure of the compound was confirmed by NMR and LC-MS to be the target product with a molecular weight of 1094.5.

[0357] Synthesis Example 3: Synthesis of Compound 64

[0358] Step 1: Synthesis of intermediate 18

[0359]

[0360] Intermediate 17 (2.93 g, 12.54 mmol), intermediate 11 (3.9 g, 11.4 mmol), Pd(dppf)Cl2 (439 mg, 0.6 mmol) and K2CO3 (4.73 g, 34.2 mmol) were mixed in dioxane / water (42 mL / 14 mL), replaced with nitrogen, and reacted at room temperature overnight. The mixture was filtered through diatomaceous earth, and EA was added to extract three times. The organic phases were combined, concentrated, and then column chromatographed to obtain intermediate 18 (3 g, yield 63.7%).

[0361] Step 2: Synthesis of intermediate 20

[0362]

[0363] Intermediate 18 (3.8 g, 9.2 mmol) was added to a mixture of 12N HCl (7.6 mL) and MeOH (20 mL) and reacted at 54°C for 2 hours. After TLC detection showed that the reaction was complete, the mixture was cooled to room temperature, saturated NaHCO3 solution was added thereto to adjust the Ph to about 7-8, and the mixture was extracted three times with EA. The organic phases were combined, washed with saturated sodium chloride aqueous solution, and concentrated to obtain a crude product of intermediate 19, which was directly used in the next step without further purification. The crude product of intermediate 19 (2.6 g, 7.2 mmol), CuBr (103 mg, 0.72 mmol), 2,2,6,6-tetramethyl-3,5-heptanedione (1.06 g, 5.76 mmol) and Cs2CO3 (5.87 g, 18 mmol) were mixed in DMF (72 mL), replaced with nitrogen, reacted overnight, cooled to room temperature, the product was filtered out, the filter cake was washed with an appropriate amount of DMF, and then washed with EtOH and PE, and dried to obtain intermediate 20 (1.85 g, two-step yield 63%).

[0364] Step 3: Synthesis of intermediate 21

[0365]

[0366] Intermediate 20 (1.85 g, 5.82 mmol), isobutylboronic acid (1.19 g, 11.64 mmol), Pd(OAc)2 (65 mg, 0.29 mmol), sphos (238 mg, 0.58 mmol) and K3PO4·3H2O (4.66 g, 17.5 mmol) were mixed in toluene (58 mL) and refluxed at 120° C. under nitrogen protection. After HPLC detection of complete conversion of intermediate 21, it was cooled to room temperature, the reaction solution was filtered through diatomaceous earth, concentrated and column chromatographed to obtain intermediate 21 (1.3 g yellow solid, yield 66%).

[0367] Step 4: Synthesis of compound 64:

[0368]

[0369] Intermediate 21 (825 mg, 2.42 mmol), IrCl3·3H2O (286 mg, 0.81 mmol), ethoxyethanol (11.5 mL) and water (3.5 mL) were weighed into a 100 mL single-necked bottle. After replacing nitrogen, the mixture was refluxed at 130°C for 24 hours. After the reaction was cooled to room temperature, the generated precipitate was filtered out, the filter cake was washed with ethanol and dried, and the obtained iridium dimer was mixed with 3,7-diethyl-1,1,1-trifluorononane-4,6-dione (319 mg, 1.2 mmol), K2CO3 (560 mg, 4.05 mmol) and ethoxyethanol (13 mL) in a 100 mL single-necked bottle. After replacing nitrogen, the mixture was reacted at room temperature overnight. After the reaction was completed as monitored by TLC, stirring was stopped. The reaction solution was filtered through diatomaceous earth, the filter cake was washed with an appropriate amount of EtOH, the crude product was washed with DCM and put into a 250 mL eggplant-shaped bottle, EtOH (about 5 mL) was added thereto, and DCM was removed by rotation at room temperature, and solid precipitation was observed, which was filtered out and washed with an appropriate amount of EtOH to obtain the product compound 64 (80 mg, yield 8.7%). The product was confirmed to be the target product with a molecular weight of 1136.4.

[0370] Synthesis Example 4: Synthesis of Compound 93

[0371] Step 1: Synthesis of iridium dimer:

[0372]

[0373] A mixture of intermediate 22 (0.76 g, 1.92 mmol), iridium trichloride trihydrate (226 mg, 0.64 mmol), 2-ethoxyethanol (7.5 mL) and water (2.5 mL) was refluxed under nitrogen for 24 hours. After cooling to room temperature, the water in the solution was carefully removed on a rotary evaporator to obtain an ethoxyethanol solution of iridium dimer, which was used directly in the next step without further purification.

[0374] Step 2: Synthesis of compound 93

[0375]

[0376] The ethoxyethanol solution of the iridium dimer obtained in the previous step, 3.7-diethyl-3-methylnonane-4,6-dione (450 mg, 1.84 mmol) and potassium carbonate (0.64 g, 4.45 mmol) were added to a 25 mL round-bottom flask and reacted at 50 ° C for 24 hours under nitrogen protection. It was then poured into a funnel filled with diatomaceous earth and filtered and washed with ethanol. Dichloromethane was added to the obtained solid and the filtrate was collected. Ethanol was then added and the obtained solution was concentrated, but not concentrated to dryness. After filtration, 550 mg of product compound 93 was obtained with a yield of 71%. The structure of the compound was confirmed by LC-MS to be the target product with a molecular weight of 1206.6.

[0377] Synthesis Example 5: Synthesis of Compound 117

[0378] Step 1: Synthesis of iridium dimer:

[0379]

[0380] Intermediate 23 (2.1 g, 5.56 mmol), iridium trichloride trihydrate (494 mg, 1.4 mmol), ethoxyethanol (18 mL) and water (6 mL) were weighed into a 250 mL single-necked bottle. After nitrogen was replaced, the mixture was refluxed at 130 ° C for 24 hours. After the reaction was cooled to room temperature, the generated precipitate was filtered out, and the filter cake was washed with ethanol and dried to obtain iridium dimer, which can be directly used in the next step without further purification.

[0381] Step 2: Synthesis of compound 117:

[0382]

[0383] The obtained iridium dimer was mixed with 3,7-diethyl-3,7-dimethyl-4,6-nonanedione (421 mg, 1.75 mmol), potassium carbonate (1.94 mg, 14 mmol) and ethoxyethanol (24 mL) in a 100 mL single-mouth bottle. After replacing nitrogen, the mixture was reacted at 55°C overnight. After TLC monitoring, the stirring was stopped. The reaction solution was filtered through diatomaceous earth, the filter cake was washed with an appropriate amount of ethanol, and the crude product was washed with dichloromethane into a 250 mL eggplant-shaped bottle. Ethanol (about 5 mL) was added thereto, and dichloromethane was removed by rotary evaporation at room temperature. Solids were precipitated, which were filtered out, washed with an appropriate amount of ethanol, dried, dissolved in dichloromethane, concentrated, and then column chromatographed to obtain red solid compound 117 (1 g, yield 60%) with a purity of 99.4%. The structure of the compound was confirmed by LC-MS to be the target product with a molecular weight of 1192.6.

[0384] Synthesis Example 6: Synthesis of Compound 116

[0385] Step 1: Synthesis of iridium dimer:

[0386]

[0387] A mixture of intermediate 24 (1.37 g, 3.73 mmol), iridium trichloride trihydrate (329 mg, 0.93 mmol), 2-ethoxyethanol (12 mL) and water (4 mL) was refluxed under nitrogen atmosphere for 24 hours. After cooling to room temperature, the red solid iridium dimer was filtered and used directly in the next step without further purification.

[0388] Step 2: Synthesis of compound 116:

[0389]

[0390] The iridium dimer obtained in the previous step, 3.7-diethyl-3,7-dimethylnonane-4,6-dione (430 mg, 1.79 mmol) and potassium carbonate (0.62 g, 4.48 mmol) were added to a 50 mL round-bottom flask and reacted at 50 ° C for 24 hours under nitrogen protection. It was then poured into a funnel filled with diatomaceous earth and filtered and washed with ethanol. Dichloromethane was added to the obtained solid and the filtrate was collected. Ethanol was then added and the obtained solution was concentrated, but not concentrated to dryness. After filtration, 810 mg of product compound 116 was obtained with a yield of 82.2%. The structure of the compound was confirmed by LC-MS to be the target product with a molecular weight of 1164.5.

[0391] Synthesis Example 7: Synthesis of Compound 261

[0392] Step 1: Synthesis of iridium dimer:

[0393]

[0394] A mixture of intermediate 25 (0.76 g, 1.92 mmol), iridium trichloride trihydrate (226 mg, 0.64 mmol), 2-ethoxyethanol (7.5 mL) and water (2.5 mL) was refluxed under nitrogen atmosphere for 24 hours. After cooling to room temperature, the water in the solution was carefully removed on a rotary evaporator to obtain an ethoxyethanol solution of iridium dimer, which was directly used in the next step without further purification.

[0395] Step 2: Synthesis of compound 261:

[0396]

[0397] The ethoxyethanol solution of the iridium dimer obtained in the previous step, 3,7-diethyl-3,7-dimethylnonane-4,6-dione (450 mg, 1.84 mmol) and potassium carbonate (0.64 g, 4.45 mmol) were added to a 25 mL round-bottom flask and reacted at 50 ° C for 24 hours under nitrogen protection. It was then poured into a funnel filled with diatomaceous earth and filtered and washed with ethanol. Dichloromethane was added to the obtained solid and the filtrate was collected. Ethanol was then added and the obtained solution was concentrated, but not concentrated to dryness. After filtration, 1.75 g of product compound 261 was obtained with a yield of 96%. The structure of the compound was confirmed by LC-MS to be the target product with a molecular weight of 1220.6.

[0398] Synthesis Example 8: Synthesis of Compound 262

[0399] Step 1: Synthesis of iridium dimer:

[0400]

[0401] A mixture of intermediate 26 (0.76 g, 1.92 mmol), iridium trichloride trihydrate (226 mg, 0.64 mmol), 2-ethoxyethanol (7.5 mL) and water (2.5 mL) was refluxed under nitrogen atmosphere for 24 hours. After cooling to room temperature, the water in the solution was carefully removed on a rotary evaporator to obtain an ethoxyethanol solution of iridium dimer, which was used directly in the next step without further purification.

[0402] Step 2: Synthesis of compound 262:

[0403]

[0404] The ethoxyethanol solution of iridium dimer obtained in the previous step, 3.7-diethyl-1,1,1-trifluorononane-4,6-dione (450 mg, 1.84 mmol) and potassium carbonate (0.64 g, 4.45 mmol) were added to a 25 mL round-bottom flask and reacted at 50 ° C for 24 hours under nitrogen protection. It was then poured into a funnel filled with diatomaceous earth and filtered and washed with ethanol. Dichloromethane was added to the obtained solid and the filtrate was collected. Ethanol was then added and the obtained solution was concentrated, but not concentrated to dryness. After filtration, 1.35 g of product compound 262 was obtained with a purity of 98.86% and a yield of 92%. The structure of the compound was confirmed by LC-MS to be the target product with a molecular weight of 1246.5.

[0405] Synthesis Example 9: Synthesis of Compound 264

[0406] Step 1: Synthesis of iridium dimer:

[0407]

[0408] Intermediate 27 (800 mg, 2.1 mmol), iridium trichloride trihydrate (250 mg, 0.7 mmol), ethoxyethanol (7.5 mL) and water (2.5 mL) were added to a 100 mL single-necked bottle. After nitrogen was replaced, the mixture was refluxed at 130 ° C for 24 hours. After the reaction was cooled, the solvent was concentrated and dried to obtain iridium dimer, which could be directly used in the next step without further purification.

[0409] Step 2: Synthesis of compound 264:

[0410]

[0411] The iridium dimer obtained in the previous step was added with 3,7-diethyl-3,7-dimethylnonane-4,6-dione (337 mg, 1.4 mmol), potassium carbonate (967 mg, 7 mmol) and ethoxyethanol (14 mL). After replacing nitrogen, the mixture was reacted at room temperature for 48 hours. The reaction solution was filtered through diatomaceous earth, the filter cake was washed with an appropriate amount of ethanol, and the crude product was washed with dichloromethane into a 250 mL eggplant-shaped bottle. Ethanol (about 5 mL) was added thereto, and dichloromethane was removed by rotary evaporation at room temperature. Solids were precipitated, which were filtered out, washed with an appropriate amount of ethanol, dried, dissolved in dichloromethane, concentrated, and purified by column chromatography to obtain compound 264 (570 mg). The structure of the compound was confirmed by LC-MS to be the target product with a molecular weight of 1192.6.

[0412] Synthesis Example 10: Synthesis of Compound 263

[0413] Step 1: Synthesis of iridium dimer:

[0414]

[0415] A mixture of intermediate 28 (0.46 g, 1.28 mmol), iridium trichloride trihydrate (130 mg, 0.37 mmol), 2-ethoxyethanol (4.5 mL) and water (1.5 mL) was refluxed under nitrogen atmosphere for 24 hours. After cooling to room temperature, the red solid iridium dimer was filtered and used directly in the next step without further purification.

[0416] Step 2: Synthesis of compound 263:

[0417]

[0418] The iridium dimer obtained in the previous step, 3.7-diethyl-3,7-dimethylnonane-4,6-dione (133 mg, 0.55 mmol) and potassium carbonate (0.25 g, 1.84 mmol) were added to a 50 mL round-bottom flask and reacted at 40 ° C for 24 hours under nitrogen protection. It was then poured into a funnel filled with diatomaceous earth and filtered and washed with ethanol. Dichloromethane was added to the obtained solid and the filtrate was collected. Ethanol was then added and the obtained solution was concentrated, but not concentrated to dryness. After filtration, 300 mg of product compound 263 was obtained with a yield of 73.7%. The structure of the compound was confirmed by LC-MS to be the target product with a molecular weight of 1164.5.

[0419] Synthesis Example 11: Synthesis of Compound 266

[0420] Step 1: Synthesis of iridium dimer:

[0421]

[0422] A mixture of intermediate 29 (1.45 g, 3.42 mmol), iridium trichloride trihydrate (346 mg, 0.98 mmol), 2-ethoxyethanol (12 mL) and water (4 mL) was refluxed under nitrogen atmosphere for 24 hours. After cooling to room temperature, the red solid iridium dimer was filtered and used directly in the next step without further purification.

[0423] Step 2: Synthesis of compound 266:

[0424]

[0425] The iridium dimer obtained in the previous step (0.67 g, 0.31 mmol), 3,7-diethyl-3-methylnonane-4,6-dione (0.21 g, 0.94 mmol) and potassium carbonate (0.43 g, 3.1 mmol) were dissolved in 9 mL of ethoxyethanol and reacted at 40 ° C for 24 hours under nitrogen protection. It was then poured into a funnel filled with diatomaceous earth and filtered and washed with ethanol. Dichloromethane was added to the obtained solid and the filtrate was collected. Ethanol was then added and the obtained solution was concentrated, but not concentrated to dryness. After filtration, 370 mg of compound 266 was obtained with a yield of 47.3%. The structure of the compound was confirmed by LC-MS to be the target product with a molecular weight of 1262.6.

[0426] Synthesis Example 12: Synthesis of Compound 265

[0427] Step 1: Synthesis of compound 265:

[0428]

[0429] Iridium dimer (0.67 g, 0.31 mmol), intermediate 30 (0.21 g, 0.94 mmol) and potassium carbonate (0.43 g, 3.1 mmol) were dissolved in 9 mL of ethoxyethanol and reacted at 40 ° C for 24 hours under nitrogen protection. It was then poured into a funnel filled with diatomaceous earth and filtered and washed with ethanol. Dichloromethane was added to the resulting solid and the filtrate was collected. Ethanol was then added and the resulting solution was concentrated, but not concentrated to dryness. After filtration, 370 mg of compound 265 was obtained with a yield of 47.3%. The structure of the compound was confirmed by LC-MS to be the target product with a molecular weight of 1302.6.

[0430] Synthesis Example 13: Synthesis of Compound 267

[0431] Step 1: Synthesis of iridium dimer:

[0432]

[0433] A mixture of intermediate 31 (0.6 g, 1.68 mmol), iridium trichloride trihydrate (198 mg, 0.56 mmol), 2-ethoxyethanol (7.5 mL) and water (2.5 mL) was refluxed under nitrogen atmosphere for 24 hours. After cooling to room temperature, the red solid iridium dimer was filtered and used directly in the next step without further purification.

[0434] Step 2: Synthesis of compound 267:

[0435]

[0436] The iridium dimer obtained in the previous step, 3,7-diethyl-3,7-dimethylnonane-4,6-dione (270 mg, 1.12 mmol) and potassium carbonate (0.77 g, 5.6 mmol) were added to a 25 mL round-bottom flask and reacted at 50 ° C for 24 hours under nitrogen protection. It was then poured into a funnel filled with diatomaceous earth and filtered and washed with ethanol. Dichloromethane was added to the obtained solid and the filtrate was collected. Ethanol was then added and the obtained solution was concentrated, but not concentrated to dryness. After filtration, 0.4 g of crude product was obtained with a purity of 91.6%. The product was further purified by column chromatography to obtain 0.3 g of the final product compound 267 with a yield of 47%. The structure of the compound was confirmed as the target product by LC-MS, with a molecular weight of 1136.5.

[0437] Synthesis Example 14: Synthesis of Compound 269

[0438] Step 1: Synthesis of iridium dimer

[0439]

[0440] A mixture of intermediate 32 (1.5 g, 4.2 mmol), iridium trichloride trihydrate (427 mg, 1.2 mmol), 2-ethoxyethanol (12 mL) and water (4 mL) was refluxed under nitrogen for 24 hours. After cooling to room temperature, the red solid iridium dimer was filtered and used directly in the next step without further purification.

[0441] Step 2: Synthesis of compound 269

[0442]

[0443] The iridium dimer obtained in the previous step, 3,7-diethyl-3,7-dimethylnonane-4,6-dione (580 mg, 2.4 mmol) and potassium carbonate (0.83 g, 6.04 mmol) were dissolved in 16 mL of ethoxyethanol and reacted at 40 ° C for 24 hours under nitrogen protection. It was then poured into a funnel filled with diatomaceous earth and filtered and washed with ethanol. Dichloromethane was added to the obtained solid and the filtrate was collected. Ethanol was then added and the obtained solution was concentrated, but not concentrated to dryness. After filtration, 940 mg of compound 269 was obtained with a yield of 66%. The structure of the compound was confirmed by LC-MS to be the target product with a molecular weight of 1166.5.

[0444] Synthesis Example 15: Synthesis of Compound 288

[0445] Step 1: Synthesis of iridium dimer:

[0446]

[0447] A mixture of intermediate 33 (1.2 g, 2.93 mmol), iridium trichloride trihydrate (427 mg, 1.2 mmol), 2-ethoxyethanol (12 mL) and water (4 mL) was refluxed under nitrogen atmosphere for 24 hours. After cooling to room temperature, the red solid iridium dimer was filtered and used directly in the next step without further purification.

[0448] Step 2: Synthesis of compound 288:

[0449]

[0450] The iridium dimer (0.67 g, 0.31 mmol), intermediate 34 (414 mg, 1.76 mmol) obtained in the previous step and sodium hydroxide (176 mg, 4.4 mmol) were dissolved in 16 mL of ethoxyethanol and reacted at 40 ° C for 24 hours under nitrogen protection. It was then poured into a funnel filled with diatomaceous earth and filtered and washed with ethanol. Dichloromethane was added to the obtained solid and the filtrate was collected. Ethanol was then added and the obtained solution was concentrated, but not concentrated to dryness. After filtration, 410 mg of compound 288 was obtained with a yield of 27.4%. The structure of the compound was confirmed by LC-MS to be the target product with a molecular weight of 1248.6.

[0451] Synthesis Example 16: Synthesis of Compound 273

[0452] Step 1: Synthesis of iridium dimer:

[0453]

[0454] A mixture of intermediate 35 (1.3 g, 3.54 mmol), iridium trichloride trihydrate (204 mg, 0.58 mmol), 2-ethoxyethanol (18 mL) and water (6 mL) was refluxed under nitrogen for 24 hours. After cooling to room temperature, the red solid iridium dimer was filtered and used directly in the next step without further purification.

[0455] Step 2: Synthesis of compound 273:

[0456]

[0457] The iridium dimer obtained in the previous step, 3,7-diethyl-3,7-dimethylnonane-4,6-dione (0.21 g, 0.87 mmol) and potassium carbonate (0.40 g, 2.9 mmol) were added to a 100 mL round-bottom flask and reacted at 50 ° C for 24 hours under nitrogen protection. It was then poured into a funnel filled with diatomaceous earth, filtered and washed with ethanol. Dichloromethane was added to the obtained solid and the filtrate was collected. Ethanol was then added and the obtained solution was concentrated, but not concentrated to dryness. After filtration, 0.7 g of crude product was obtained, which was further purified by column chromatography to obtain 0.6 g of compound 273 with a yield of 91%. The structure of the compound was confirmed as the target product by LC-MS, with a molecular weight of 1136.5.

[0458] Synthesis Example 17: Synthesis of Compound 282

[0459] Step 1: Synthesis of iridium dimer:

[0460]

[0461] A mixture of intermediate 36 (1.77 g, 3.87 mmol), iridium trichloride trihydrate (390 mg, 1.11 mmol), 2-ethoxyethanol (24 mL) and water (8 mL) was refluxed under nitrogen atmosphere for 24 hours. After cooling to room temperature, the red solid iridium dimer was filtered and used directly in the next reaction without further purification.

[0462] Step 2: Synthesis of compound 282:

[0463]

[0464] The iridium dimer obtained in the previous step, 3,7-diethyl-3,7-dimethylnonane-4,6-dione (0.4 g, 1.66 mmol) and potassium carbonate (0.77 mg, 5.6 mmol) were added to a 100 mL round-bottom flask and reacted at 50 ° C for 48 hours under nitrogen protection. It was then poured into a funnel filled with diatomaceous earth, filtered and washed with ethanol. Dichloromethane was added to the obtained solid and the filtrate was collected. Ethanol was then added and the obtained solution was concentrated, but not concentrated to dryness. After filtration, 0.7 g of crude product was obtained, which was further purified by column chromatography to obtain 0.25 g of compound 282 with a yield of 17%. The structure of the compound was confirmed as the target product by LC-MS, with a molecular weight of 1344.6.

[0465] Synthesis Example 18: Synthesis of Compound 287

[0466] Step 1: Synthesis of compound 287:

[0467]

[0468] Iridium dimer (0.94 g, 0.45 mmol), 3,7-diethyl-3,7-dimethylnonane-4,6-dione (0.32 g, 1.34 mmol) and potassium carbonate (0.62 mg, 4.45 mmol) were dissolved in 25 mL of ethoxyethanol and reacted at 40 ° C for 24 hours under nitrogen protection. It was then poured into a funnel filled with diatomaceous earth and filtered and washed with ethanol. Dichloromethane was added to the obtained solid and the filtrate was collected. Ethanol was then added and the obtained solution was concentrated, but not concentrated to dryness. After filtration, 0.87 g of compound 287 was obtained with a yield of 78%. The structure of the compound was confirmed by LC-MS to be the target product with a molecular weight of 1248.6.

[0469] Synthesis Example 19: Synthesis of Compound 291

[0470] Step 1: Synthesis of intermediate 38

[0471]

[0472] Intermediate 37 (2.68 g, 8.69 mmol) and TMEDA (1.31 g, 11.3 mmol) were dissolved in 80 mL of ultra-dry THF, the reaction system was cooled to 0°C, and then n-butyl lithium (4.2 mL, 10.43 mmol, 2.5 M) was slowly added. After reacting at this temperature for 1 h, isopropanol pinacol borate (2.102 g, 11.3 mmol) was added and the reaction was allowed to proceed overnight. When TLC showed that the reaction was complete, saturated ammonium chloride was added to quench the reaction, and the reaction was extracted with EA. The product was dried, filtered, and evaporated to remove the solvent to obtain a crude product, which was purified by silica gel column chromatography to obtain intermediate 38 (3.86 g, 82%).

[0473] Step 2: Synthesis of intermediate 39

[0474]

[0475] A mixture of intermediate 12 (1.95 g, 8.4 mmol), intermediate 38 (3.85 g, 8.4 mmol), Pd(PPh3)4 (0.48 g, 0.42 mmol), sodium carbonate (1.34 g, 12.6 mmol) and 1,4-dioxane / water (32 mL / 8 mL) was heated to reflux overnight under nitrogen protection, and cooled to room temperature after TLC showed that the reaction was complete. Water was added to the reaction system, the organic phase was extracted with EA, dried and filtered, and the solvent was removed by rotary evaporation to obtain intermediate 39 (3.1 g, yield 70%).

[0476] Step 3: Synthesis of intermediate 40

[0477]

[0478] Intermediate 39 (3.1 g, 5.91 mmol) was dissolved in 15 mL of ethanol, and then 15 mL of HCl (2N) was slowly added to the reaction system, followed by heating to reflux and reacting for 2 h. After TLC showed that the reaction was completed, it was cooled to room temperature, and sodium bicarbonate solution was added to neutralize to neutrality. The solid crude product was filtered to obtain the intermediate 40 (2.75 g, yield 99.78%).

[0479] Step 4: Synthesis of intermediate 41

[0480]

[0481] Intermediate 40 (2.75 g, 5.9 mmol), cuprous bromide (86 mg, 0.6 mmol), 2,2,6,6-tetramethylheptanedione (0.88 g, 4.8 mmol), cesium carbonate (4.89 g, 15 mmol) and DMF (60 mL) were heated to 135 ° C under nitrogen protection for overnight reaction, and cooled to room temperature after TLC showed that the reaction was complete. Water was added until a large amount of yellow solid precipitated in the solution, filtered, and the solid was washed with water several times and then dried to obtain yellow solid intermediate 41 (2.54 g, yield 99.8%).

[0482] Step 5: Synthesis of intermediate 42

[0483]

[0484] Intermediate 41 (2.54 g, 5.91 mmol), neopentylboronic acid (1.37 g, 11.83 mmol), Pd2(dba)3 (135 mg, 0.15 mmol), Sphos (243 mg, 0.59 mmol), K3PO4.3H2O (4.72 g, 17.7 mmol) and 30 mL of toluene were mixed, the system was evacuated and replaced with nitrogen three times, heated to reflux, and reacted overnight. After TLC detection, the reaction was completed and then cooled to room temperature. The solvent was removed by rotary evaporation to obtain a crude product, which was purified by column chromatography to obtain intermediate 42 (1.8 g, yield 65%).

[0485] Step 6: Synthesis of iridium dimer:

[0486]

[0487] A mixture of intermediate 42 (1.4 g, 3.0 mmol), iridium trichloride trihydrate (0.35 g, 1.0 mmol), 2-ethoxyethanol (12 mL) and water (4 mL) was refluxed under nitrogen atmosphere for 24 hours. After cooling to room temperature, the red solid iridium dimer was filtered and used directly in the next reaction without further purification.

[0488] Step 7: Synthesis of compound 291:

[0489]

[0490] The iridium dimer obtained in the previous step, 3.7-diethyl-1,1,1-trifluorononane-4,6-dione (0.39 g, 1.5 mmol) and potassium carbonate (0.69 g, 5.00 mmol) were dissolved in 16 mL of ethoxyethanol and reacted at 50 ° C for 24 hours under nitrogen protection. It was then poured into a funnel filled with diatomaceous earth and filtered and washed with ethanol. Dichloromethane was added to the obtained solid and the filtrate was collected. Ethanol was then added and the obtained solution was concentrated, but not concentrated to dryness. After filtration, 0.71 g of compound 291 was obtained with a yield of 41.2%. The structure of the compound was confirmed by LC-MS to be the target product with a molecular weight of 1386.7.

[0491] Synthesis Example 20: Synthesis of Compound 292

[0492] Step 1: Synthesis of iridium dimer:

[0493]

[0494] A mixture of intermediate 43 (1.4 g, 2.92 mmol), iridium trichloride trihydrate (0.34 g, 0.97 mmol), 2-ethoxyethanol (12 mL) and water (4 mL) was refluxed under nitrogen atmosphere for 24 hours. After cooling to room temperature, the red solid iridium dimer was filtered and used directly in the next step without further purification.

[0495] Step 2: Synthesis of compound 292:

[0496]

[0497] The iridium dimer obtained in the previous step, 3.7-diethyl-1,1,1-trifluorononane-4,6-dione (0.38 g, 1.5 mmol) and potassium carbonate (0.67 g, 4.85 mmol) were dissolved in 16 mL of ethoxyethanol and reacted at 50 ° C for 24 hours under nitrogen protection. It was then poured into a funnel filled with diatomaceous earth and filtered and washed with ethanol. Dichloromethane was added to the obtained solid and the filtrate was collected. Ethanol was then added and the obtained solution was concentrated, but not concentrated to dryness. After filtration, 0.67 g of compound 292 was obtained with a yield of 49%. The structure of the compound was confirmed by LC-MS to be the target product with a molecular weight of 1414.7.

[0498] Synthesis Example 21: Synthesis of Compound 293

[0499] Step 1: Synthesis of compound 293:

[0500]

[0501] Iridium dimer (1.01 g, 0.97 mmol), 3,3,7-triethylnonane-4,6-dione (0.4 g, 1.5 mmol) and potassium carbonate (0.72 g, 4.85 mmol) were dissolved in 16 mL of ethoxyethanol and reacted at 50 ° C for 24 hours under nitrogen protection. It was then poured into a funnel filled with diatomaceous earth and filtered and washed with ethanol. Dichloromethane was added to the resulting solid and the filtrate was collected. Ethanol was then added and the resulting solution was concentrated, but not concentrated to dryness. After filtration, 0.62 g of compound 293 was obtained with a yield of 45%. The structure of the compound was confirmed by LC-MS to be the target product with a molecular weight of 1388.8.

[0502] Synthesis Example 22: Synthesis of Compound 294

[0503] Step 1: Synthesis of iridium dimer:

[0504]

[0505] A mixture of intermediate 44 (0.68 g, 1.60 mmol), iridium trichloride trihydrate (0.16 g, 0.45 mmol), 2-ethoxyethanol (6 mL) and water (2 mL) was refluxed under nitrogen atmosphere for 24 hours. After cooling to room temperature, the red solid iridium dimer was filtered and used directly in the next reaction without further purification.

[0506] Step 2: Synthesis of compound 294:

[0507]

[0508] The iridium dimer obtained in the previous step, 3,7-diethyl-3,7-dimethylnonane-4,6-dione (0.22 g, 0.9 mmol) and potassium carbonate (0.62 g, 4.5 mmol) were dissolved in 16 mL of ethoxyethanol and reacted at 50 ° C for 24 hours under nitrogen protection. It was then poured into a funnel filled with diatomaceous earth and filtered and washed with ethanol. Dichloromethane was added to the obtained solid and the filtrate was collected. Ethanol was then added and the obtained solution was concentrated, but not concentrated to dryness. After filtration, 0.42 g of compound 294 was obtained with a yield of 73%. The structure of the compound was confirmed by LC-MS to be the target product with a molecular weight of 1276.7.

[0509] Synthesis Example 23: Synthesis of Compound 295

[0510] Step 1: Synthesis of iridium dimer:

[0511]

[0512] A mixture of intermediate 45 (2.03 g, 4.93 mmol), iridium trichloride trihydrate (0.48 g, 1.37 mmol), 2-ethoxyethanol (33 mL) and water (11 mL) was refluxed under nitrogen atmosphere for 24 hours. After cooling to room temperature, the red solid iridium dimer was filtered and used directly in the next step without further purification.

[0513] Step 2: Synthesis of compound 295:

[0514]

[0515] The iridium dimer obtained in the previous step, 3,7-diethyl-1,1,1-trifluorononane-4,6-dione (0.53 g, 2 mmol) and potassium carbonate (0.95 g, 6.85 mmol) were mixed in ethoxyethanol (23 mL), replaced with nitrogen, and reacted at room temperature for 48 hours. The reaction solution was filtered through diatomaceous earth, the filter cake was washed with an appropriate amount of EtOH, and the crude product was washed with DCM into a 250 mL eggplant-shaped bottle, EtOH (about 10 mL) was added thereto, and DCM was removed by rotary evaporation at room temperature. Solids precipitated, filtered and washed with an appropriate amount of EtOH to obtain a crude product, which was purified by column chromatography to obtain 0.1 g of compound 295 with a yield of 5.7%. The structure of the compound was confirmed by LC-MS to be the target product with a molecular weight of 1278.5.

[0516] Synthesis Example 24: Synthesis of Compound 280

[0517] Step 1: Synthesis of iridium dimer:

[0518]

[0519] At room temperature, the intermediate 46 (0.15 g, 0.526 mmol) raw material was dissolved in 9 mL 2-ethoxyethanol and 3 mL water, and IrCl3·3H2O (62 mg, 0.175 mmol) was added, and the mixture was heated to 160°C in an autoclave, refluxed at this temperature for 24 hours, and cooled to room temperature. The mixture was filtered, and the solid was washed with ethanol until the washing liquid was colorless, and the red solid iridium dimer was obtained by suction filtration, which could be directly used in the next step without purification.

[0520] Step 2: Synthesis of compound 280:

[0521]

[0522] The iridium dimer (0.25 g, 0.157 mmol) obtained in the previous step was added to a 100 mL round-bottom flask, K2CO3 (217 mg, 1.57 mmol) and 3,7-diethyl-3-methylnonane-4,6-dione (142 mg, 0.629 mmol) were added, 5 mL of 2-ethoxyethanol and 5 mL of DCM were added, and the mixture was ventilated three times at room temperature, heated to 40 ° C, and stirred for 24 hours under nitrogen protection. DCM was removed by vacuum, filtered with diatomaceous earth, and the solid was washed with ethanol until the washing liquid was colorless, and ethanol was removed by suction. Under vacuum filtration, the red solid on the diatomaceous earth was dissolved in 200 mL of dichloromethane, 20 mL of ethanol was added, and dichloromethane was removed by vacuum. The solid precipitated and filtered to obtain red solid compound 280 (195 mg, 0.20 mmol, yield 63.7%). The structure of the compound was confirmed as the target product by LC-MS, with a molecular weight of 986.3.

[0523] Synthesis Example 25: Comprising Ligand L a1931 Synthesis of compounds

[0524] Step 1: Synthesis of intermediate 48

[0525]

[0526] A mixture of intermediate 12 (1.63 g, 7.0 mmol), intermediate 47 (3.9 g, 7.4 mmol), Pd(PPh3)4 (0.4 g, 0.35 mmol), sodium carbonate (1.11 g, 10.5 mmol) and 1,4-dioxane / water (28 mL / 7 mL) was heated to reflux overnight under nitrogen protection, and cooled to room temperature after TLC showed that the reaction was complete. Water was added to the reaction system, the organic phase was extracted with EA, dried and filtered, and the solvent was removed by rotary evaporation to obtain intermediate 48 (3.2 g, yield 76%).

[0527] Step 2: Synthesis of intermediate 49

[0528]

[0529] Intermediate 48 (3.2 g, 5.33 mmol) was dissolved in 15 mL of ethanol, and then 15 mL of HCl (2N) was slowly added to the reaction system, followed by heating to reflux and reacting for 2 h. After TLC showed that the reaction was completed, it was cooled to room temperature, and sodium bicarbonate solution was added to neutralize to neutrality. The solid crude product was filtered to obtain the intermediate 49 (2.65 g, yield 94.5%).

[0530] Step 3: Synthesis of intermediate 50

[0531]

[0532] Intermediate 49 (2.65 g, 5.0 mmol), cuprous bromide (72 mg, 0.5 mmol), 2,2,6,6-tetramethylheptanedione (0.74 g, 4.0 mmol), cesium carbonate (4.07 g, 12.5 mmol) and DMF (50 mL) were heated to 135 ° C under nitrogen protection for overnight reaction, and cooled to room temperature after TLC showed that the reaction was complete. Water was added until a large amount of yellow solid precipitated in the solution, filtered, and the solid was washed with water several times and then dried to obtain yellow solid intermediate 50 (2.26 g, yield 92.4%).

[0533] Step 4: Synthesis of Intermediate 51

[0534]

[0535] Intermediate 50 (2.26 g, 4.62 mmol), neopentylboronic acid (1.07 g, 9.23 mmol), Pd2(dba)3 (106 mg, 0.12 mmol), Sphos (190 mg, 0.46 mmol), K3PO4.3H2O (3.69 g, 13.9 mmol) and 30 mL of toluene were mixed, the system was evacuated and replaced with nitrogen three times, heated to reflux, reacted overnight, cooled to room temperature after TLC detection until the reaction was complete, and the solvent was removed by rotary evaporation to obtain a crude product, which was purified by column chromatography to obtain intermediate 51 (1.8 g, yield 74%). The structure of this intermediate was confirmed to be the target structure by LC-MS, and the molecular weight was 525.3.

[0536] Starting from intermediate 51, those skilled in the art can obtain the ligand L of the present invention by referring to the methods of the prior art or according to the methods of Synthesis Examples 1-24. a1931 of compounds.

[0537] Those skilled in the art should be aware that the above preparation method is only an illustrative example, and those skilled in the art can obtain other compound structures of the present invention by improving it.

[0538] Device Embodiment

[0539] Device Example 1

[0540] First, the glass substrate with a 120nm thick indium tin oxide (ITO) anode was cleaned and then treated with oxygen plasma and UV ozone. After treatment, the substrate was dried in a glove box to remove moisture. The substrate was then mounted on a substrate holder and loaded into a vacuum chamber. The organic layers specified below were placed in a vacuum of approximately 10 -8 Compound HI is used as a hole injection layer (HIL) with a thickness of 1000 nm. Compound HT was used as a hole transport layer (HTL) with a thickness of Compound EB1 was used as an electron blocking layer (EBL) with a thickness of Then, the compound 81 of the present invention was doped in the host compound RH to serve as an emitting layer (EML, 2:98) with a thickness of Compound HB is used as a hole blocking layer (HBL) with a thickness of On the HBL, a mixture of compound ET and 8-hydroxyquinoline-lithium (Liq) was deposited as an electron transport layer (ETL) with a thickness of Finally, 1 nm thick Liq was deposited as an electron injection layer and 120 nm Al was deposited as a cathode. The device was then transferred back to the glove box and encapsulated with a glass cover and a moisture absorber to complete the device.

[0541] Device Example 2

[0542] The preparation method of device example 2 is the same as that of device example 1, except that compound 83 of the present invention is used instead of compound 81 of the present invention in the light emitting layer (EML).

[0543] Device Example 3

[0544] The preparation method of device example 3 is the same as that of device example 1, except that compound 64 of the present invention is used instead of compound 81 of the present invention in the light-emitting layer (EML), the doping ratio of compound 64 of the present invention to compound RH is adjusted to 3:97, and compound EB2 is used instead of compound EB1 in the electron blocking layer (EBL).

[0545] Device Example 4

[0546] The preparation method of device example 4 is the same as that of device example 3, except that compound 93 of the present invention is used instead of compound 64 of the present invention in the light emitting layer (EML).

[0547] Device Example 5

[0548] The preparation method of device example 5 is the same as that of device example 3, except that the compound 117 of the present invention is used instead of the compound 64 of the present invention in the light emitting layer (EML).

[0549] Device Example 6

[0550] The preparation method of device example 6 is the same as that of device example 3, except that the compound 116 of the present invention is used instead of the compound 64 of the present invention in the light emitting layer (EML).

[0551] Device Example 7

[0552] The preparation method of device example 7 is the same as that of device example 3, except that the compound 261 of the present invention is used instead of the compound 64 of the present invention in the light emitting layer (EML).

[0553] Device Example 8

[0554] The preparation method of device example 8 is the same as that of device example 3, except that compound 262 of the present invention is used instead of compound 64 of the present invention in the light emitting layer (EML).

[0555] Device Example 9

[0556] The preparation method of device example 9 is the same as that of device example 3, except that compound 264 of the present invention is used instead of compound 64 of the present invention in the light emitting layer (EML).

[0557] Device Example 10

[0558] The preparation method of device example 10 is the same as that of device example 3, except that the compound 263 of the present invention is used instead of the compound 64 of the present invention in the light emitting layer (EML).

[0559] Device Example 11

[0560] The preparation method of device example 11 is the same as that of device example 3, except that the compound 266 of the present invention is used instead of the compound 64 of the present invention in the light emitting layer (EML).

[0561] Device Example 12

[0562] The preparation method of device example 12 is the same as that of device example 3, except that the compound 265 of the present invention is used instead of the compound 64 of the present invention in the light emitting layer (EML).

[0563] Device Example 13

[0564] The preparation method of device example 13 is the same as that of device example 3, except that the compound 267 of the present invention is used instead of the compound 64 of the present invention in the light emitting layer (EML).

[0565] Device Example 14

[0566] The preparation method of device example 14 is the same as that of device example 3, except that the compound 282 of the present invention is used instead of the compound 64 of the present invention in the light emitting layer (EML).

[0567] Device Example 15

[0568] The preparation method of device example 15 is the same as that of device example 3, except that the compound 273 of the present invention is used instead of the compound 64 of the present invention in the light emitting layer (EML).

[0569] Device Example 16

[0570] The preparation method of device example 16 is the same as that of device example 3, except that compound 294 of the present invention is used instead of compound 64 of the present invention in the light emitting layer (EML).

[0571] Device Example 17

[0572] The preparation method of device example 17 is the same as that of device example 3, except that the compound 287 of the present invention is used instead of the compound 64 of the present invention in the light emitting layer (EML).

[0573] Device Example 18

[0574] The preparation method of device example 18 is the same as that of device example 3, except that the compound 291 of the present invention is used instead of the compound 64 of the present invention in the light emitting layer (EML).

[0575] Device Example 19

[0576] The preparation method of device example 19 is the same as that of device example 3, except that the compound 292 of the present invention is used instead of the compound 64 of the present invention in the light emitting layer (EML).

[0577] Device Example 20

[0578] The preparation method of device example 20 is the same as that of device example 3, except that the compound 293 of the present invention is used instead of the compound 64 of the present invention in the light emitting layer (EML).

[0579] Device Example 21

[0580] The preparation method of device example 21 is the same as that of device example 3, except that the compound 295 of the present invention is used instead of the compound 64 of the present invention in the emissive layer (EML).

[0581] Device Comparison Example 1

[0582] Device Comparative Example 1 was prepared in the same manner as Device Example 1, except that Compound RD was used instead of the present compound 81 in the emission layer (EML).

[0583] Device Comparison Example 2

[0584] Device Comparative Example 2 was prepared in the same manner as Device Example 3, except that Compound RD was used instead of the present compound 64 in the emission layer (EML).

[0585] The partial layer structures and thicknesses of the device are shown in the table below. Where more than one material is used, the different compounds are doped in the weight ratios recorded.

[0586] Table 1 Partial device structures of device embodiments and comparative examples

[0587]

[0588]

[0589]

[0590] The structure of the materials used in the device is shown below:

[0591]

[0592]

[0593]

[0594]

[0595] The IVL and lifetime characteristics of the device were measured at different current densities and voltages. Table 2 shows the IVL and lifetime characteristics of the device at 15 mA / cm 2 CIE data, driving voltage (V), maximum emission wavelength (λmax), half maximum width (FWHM) and external quantum efficiency (EQE) of device example 1, device example 2 and device comparative example 1 measured under constant current, and at 80 mA / cm 2 Lifetime at constant current (LT97).

[0596] Table 2 Device data

[0597]

[0598] discuss:

[0599] From the data shown in Table 2, it can be seen that the half-peak widths of Comparative Example 1 and Examples 1 and 2 are all around 30nm, reaching a very amazing level. However, the maximum emission wavelength of Comparative Example 1 is 566nm, while in Examples 1 and 2, a significant red shift of the maximum emission wavelength is achieved through the design of the molecular structure of the luminescent dopant, making the emission wavelength between 606nm and 620nm, meeting the requirements for different bands of red emission. At 15mA / cm 2 Under constant current, both the voltage and external quantum efficiency data of Example 1 and Example 2 are superior to that of Comparative Example 1, especially the external quantum efficiency of Example 2 is 36% higher than that of Comparative Example 1. According to Comparative Example 1 and Examples 1 and 2 at 80 mA / cm 2The LT97 life data under constant current shows that the life of Comparative Example 1 under this condition is 2 hours, while that of Example 1 is 30 hours and that of Example 2 is 105 hours. It can be seen that the compounds disclosed in the present invention can significantly improve the device life in electroluminescent devices. From the above data analysis, it can be seen that the embodiments can effectively adjust the emission wavelength to meet the requirements of red light emission, reduce voltage, improve EQE, and most importantly, significantly improve the life, thereby providing excellent performance, in addition to maintaining a very narrow half-peak width.

[0600] Table 3 shows that at 15 mA / cm 2 CIE data, driving voltage (V), maximum emission wavelength (λmax), half maximum width (FWHM) and lifetime (LT97) of device Example 3 measured under constant current.

[0601] Table 3 Device data

[0602]

[0603] discuss:

[0604] From the data shown in Table 3, it can be seen that by adjusting the molecular structure, the emission wavelength of Example 3 is 633nm, which is in the deep red region, and the emission wavelength is 15mA / cm 2 Under constant current, the half-peak width of Example 3 is also very narrow, at 39 nm, and the driving voltage is relatively low, at 3.78V.

[0605] Table 4 shows that at 15 mA / cm 2 CIE data, driving voltage (V), maximum emission wavelength (λ) of device comparative example 2 and device embodiments 4 to 21 measured under constant current max ), half maximum width (FWHM) and external quantum efficiency (EQE), as well as at 80mA / cm 2 Lifetime at constant current (LT97).

[0606] Table 4 Device data

[0607]

[0608]

[0609] discuss:

[0610] It can also be found from the device data in Table 4 that in Examples 4 to 13, when the compounds of the present invention are used as dopants in the light-emitting layer, a large red shift in the maximum emission wavelength of the device is successfully achieved, and the emission wavelength is between 614nm and 623nm, which meets the requirements for different bands of red emission, while the maximum emission wavelength of Comparative Example 2 using the comparative compound RD is only 566nm, which is completely unable to meet the requirements of the red light device for the luminous color. In addition, at 15mA / cm 2 Under constant current, although the half-peak width and voltage of Examples 4 to 13 are basically the same as or slightly less than those of Comparative Example 2, it should be noted that, on the one hand, the half-peak width of less than 36nm of Examples 4 to 13 is still a very high level in the industry, and the voltage of Examples 4 to 13 is also a relatively low level in the industry. On the other hand, the external quantum efficiency data of Examples 4 to 13 are further improved compared to the already high level of Comparative Example 2. Most importantly, Examples 4 to 13 have a low external quantum efficiency of 80 mA / cm 2 The life data of LT97 under constant current has been greatly improved (the lowest is close to 20 times, the highest is close to 50 times) compared with Comparative Example 2 (the life under this condition is only 3 hours, which is completely unable to meet the demand). The above comparisons once again prove that the compounds disclosed in the present invention have very excellent performance.

[0611] It can also be found from the device data in Table 4 that in Examples 14 to 21, when the compounds of the present invention are used as dopants in the light-emitting layer, a large red shift in the maximum emission wavelength of the device is successfully achieved, and the emission wavelength is between 607nm and 625nm, which meets the requirements for different bands of red emission, while the maximum emission wavelength of Comparative Example 2 using the comparative compound RD is only 566nm, which is completely unable to meet the requirements of the red light device for the luminous color. In addition, at 15mA / cm 2 Under constant current, although the half-peak width and voltage of Examples 14 to 21 are basically the same as or slightly less than those of Comparative Example 2, it should be noted that, on the one hand, the half-peak width of less than 34nm of Examples 14 to 21 is still a very high level in the industry, and at the same time, the voltage of Examples 14 to 21 is also at a relatively low level in the industry. On the other hand, the external quantum efficiency data of Examples 14 to 21 can maintain a high level close to that of Comparative Example 2, or further improve on the already high level of Comparative Example 2. Most importantly, Examples 14 to 21 have a high power consumption of 80 mA / cm 2 The life data of LT97 under constant current has been greatly improved (9 times at the lowest and nearly 50 times at the highest) compared with Comparative Example 2 (the life under this condition is only 3 hours, which is completely unable to meet the demand). The above comparisons once again prove that the compounds disclosed in the present invention have very excellent performance.

[0612] Device Example 22

[0613] The preparation method of device example 22 is the same as that of device example 3, except that compound 280 of the present invention is used instead of compound 64 of the present invention, and compound RH2 is used instead of compound RH in the emission layer (EML).

[0614] Device Example 23

[0615] The preparation method of device example 23 is the same as that of device example 22, except that the weight ratio of the compound 280 of the present invention to the host compound RH2 in the light-emitting layer (EML) is adjusted to 2:98.

[0616] The partial layer structures and thicknesses of the device are shown in the table below. Where more than one material is used, the different compounds are doped in the weight ratios recorded.

[0617] Table 5 Partial device structures of device embodiments 22 and 23

[0618]

[0619]

[0620] The structure of the new material used in the device is shown below:

[0621]

[0622] The IVL and lifetime characteristics of the device were measured at different current densities and voltages. Table 6 shows the IVL and lifetime characteristics of the device at 15 mA / cm 2 CIE data, driving voltage (V), maximum emission wavelength (λmax), half maximum width (FWHM), and external quantum efficiency (EQE) of device examples 22 and 23 measured at constant current, and at 80 mA / cm 2 Lifetime at constant current (LT97).

[0623] Table 6 Device data

[0624]

[0625] From the data in Table 6, it can be seen that when the compound of the present invention is used as a luminescent dopant in a device, the maximum emission wavelength of the device reaches 625 nm, which meets the requirements of red light emission; at the same time, the half-peak widths of Examples 22 and 23 are both less than 30 nm, reaching a very amazing level, and can achieve very saturated luminescence; in addition, the voltages of Examples 22 and 23 are both less than 3.5 V, which is a very low voltage, and the external quantum efficiency is greater than 20%, which is a relatively high device efficiency; more importantly, Examples 22 and 23 also have very long device life. The above data once again prove that the compounds disclosed in the present invention have very excellent performance.

[0626] In summary, the compounds disclosed in the present invention can not only maintain a very narrow half-peak width, but also effectively adjust the emission wavelength to meet the requirements of red light emission, reduce the voltage or maintain a low voltage level, improve EQE, and most importantly, significantly increase the life span, thereby providing excellent performance.

[0627] According to our research on OLED red light emitting materials, in the structure of formula 1, when the substituent R is not a hydrogen atom, the emission spectrum of the material can be well adjusted and the external quantum efficiency of the material can be improved:

[0628]

[0629] However, according to our repeated studies, the ligand with the structure of formula 2 cannot successfully complex with metals to form metal complexes:

[0630]

[0631] Unexpectedly, by designing the structure, the substituent R in Formula 1 is designed to be part of a ring. On the one hand, a ligand having a corresponding structure, such as Formula 1 disclosed in the present invention, can successfully react with a metal to form a metal complex. On the other hand, the device research results of related compounds show that the metal complexes of this type of structure disclosed in the present invention exhibit excellent device performance when used as luminescent materials in electroluminescent devices, can effectively adjust the emission wavelength to meet the red light emission requirements, obtain a very narrow half-peak width, reduce the voltage or maintain a low voltage, improve EQE, and most importantly, can greatly improve the life span. These results further highlight the uniqueness and importance of the present invention.

[0632] It should be understood that the various embodiments described herein are only examples and are not intended to limit the scope of the present invention. Therefore, as will be apparent to those skilled in the art, the claimed invention may include variations of the specific embodiments and preferred embodiments described herein. Many of the materials and structures described herein may be replaced with other materials and structures without departing from the spirit of the present invention. It should be understood that the various theories about why the present invention works are not intended to be restrictive.

Claims

1. An electroluminescent device comprising an anode, a cathode, and an organic layer disposed between the anode and the cathode, wherein the organic layer comprises a metal complex comprising a ligand L a , L a Having a structure represented by Formula 1: in, Ring A and Ring B are each independently selected from a five-membered unsaturated carbocyclic ring, an aromatic ring having 6 to 30 carbon atoms, or a heteroaromatic ring having 3 to 30 carbon atoms; R i Each occurrence of R is the same or different, indicating mono-, poly- or unsubstituted; ii Each occurrence is identical or different and indicates mono-, poly-, or unsubstituted; Y is selected from SiR y R y ,GeR y R y , NR y , P.R. y , O, S or Se; When there are two R y When two R y Can be the same or different; X1-X2 are selected from CR in the same or different ways each time they appear x or N; R, R i , R ii , R x and R y Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted an alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amine group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; Adjacent substituent R i , R x , R y , R and R ii can optionally be linked to form a ring; The metal is selected from metals having a relative atomic mass greater than 40.

2. The electroluminescent device of claim 1, wherein the organic layer is a light-emitting layer, and the metal complex is a light-emitting material.

3. The electroluminescent device according to claim 1 or 2, wherein the electroluminescent device emits red light or white light.

4. The electroluminescent device of claim 2, wherein the light-emitting layer further comprises at least one host material; preferably, the at least one host material comprises at least one chemical group selected from the group consisting of benzene, pyridine, pyrimidine, triazine, carbazole, azacarbazole, indolecarbazole, dibenzothiophene, azadibenzothiophene, dibenzofuran, azadibenzofuran, dibenzoselenophene, triphenylene, azatriphenylene, fluorene, silylfluorene, naphthalene, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene, azaphenanthrene, and combinations thereof.

5. The electroluminescent device according to claim 1, wherein Ring A and / or Ring B are each independently selected from a five-membered unsaturated carbocyclic ring, an aromatic ring having 6 to 18 carbon atoms, or a heteroaromatic ring having 3 to 18 carbon atoms; Preferably, Ring A and / or Ring B are each independently selected from a five-membered unsaturated carbocyclic ring, an aromatic ring having 6 to 10 carbon atoms, or a heteroaromatic ring having 3 to 10 carbon atoms.

6. The electroluminescent device according to claim 1 or 5, wherein said L a A structure selected from any one of Formula 2 to Formula 19 and Formula 22-Formula 23: in, In Formula 2-19 and Formula 22-23, X1-X2 are selected from CR x or N; X3-X7 are selected from CR in the same or different manner each time they appear i or N; A1-A6 are selected from CR in the same or different manner each time they appear ii or N; Each time Z appears, it is selected from CR iii R iii ,SiR iii R iii , P.R. iii , O, S or NR iii ; When there are two R iii When two R iii Same or different; Y is selected from SiR y R y , NR y , P.R. y , O, S or Se; when there are two R y When two R y Same or different; R, R x , R y , R i , R ii and R iii The alkyl radicals are selected, at each occurrence, identically or differently, from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl radicals having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl radicals having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl radicals having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl radicals having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy radicals having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy radicals having 6 to 30 carbon atoms, substituted or unsubstituted substituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amine groups, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof; Adjacent substituents R, R x , R y , R i , R ii and R iii can optionally be linked to form a ring; Preferably, L a A structure selected from Formula 2, Formula 9, Formula 11 or Formula 12; More preferably, L a A structure represented by Formula 2 is selected.

7. The electroluminescent device according to claim 6, wherein: In equations 2-19 and 22-23, X1-X n and / or A1-A m At least one of the X is selected from N, n Corresponding to the largest sequence number of X1-X7 in any one of Formula 2-Formula 19 and Formula 22-Formula 23, the A m The largest sequence number corresponding to A1-A6 in any one of Formula 2-Formula 19 and Formula 22-Formula 23; Preferably, in Formula 2-Formula 19 and Formula 22-Formula 23, X1-X n At least one of the X is selected from N, n The one with the largest sequence number corresponding to X1-X7 in any one of Formula 2-Formula 19 and Formula 22-Formula 23; More preferably, X2 is N.

8. The electroluminescent device according to claim 6, wherein: In Formula 2-19 and Formula 22-23, X1-X2 are each independently selected from CR x ; X3-X7 are each independently selected from CR i ; A1-A6 are each independently selected from CR ii ; Adjacent substituent R x , R i , R ii can optionally be linked to form a ring; Preferably, the R x , R i , R ii each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, cyano, and combinations thereof; More preferably, the R x , R i , R ii At least two or three of the following are selected, at each occurrence, identically or differently, from the group consisting of deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, cyano, and combinations thereof.

9. The electroluminescent device according to any one of claims 6 to 8, wherein: In Formula 2-Formula 11 and Formula 22-Formula 23, X4 and / or X5 are selected from CR i In formula 12-19, X3 is selected from CR i ; And the R i is selected, at each occurrence, identically or differently, from hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, cyano, or a combination thereof; Preferably, the R i Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, fluorine, methyl, ethyl, isopropyl, isobutyl, tert-butyl, neopentyl, cyclopentyl, cyclopentylmethyl, cyclohexyl, norbornyl, adamantyl, trimethylsilyl, isopropyldimethylsilyl, phenyldimethylsilyl, trifluoromethyl, cyano, phenyl, and combinations thereof.

10. The electroluminescent device according to any one of claims 6 to 9, wherein: In Formulae 2-19 and 22-23, R is selected from hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, or a combination thereof; Preferably, R is selected from hydrogen, deuterium, fluorine, methyl, ethyl, isopropyl, isobutyl, tert-butyl, cyclopentyl, cyclopentylmethyl, cyclohexyl, neopentyl, deuterated methyl, deuterated ethyl, deuterated isopropyl, deuterated isobutyl, deuterated tert-butyl, deuterated cyclopentyl, deuterated cyclopentylmethyl, deuterated cyclohexyl, deuterated neopentyl, trimethylsilyl, or a combination thereof.

11. The electroluminescent device according to any one of claims 6 to 10, wherein: In Formulae 2-19 and 22-23, Y is selected from O or S; preferably, Y is O.

12. The electroluminescent device according to any one of claims 6 to 11, wherein: In Formula 2-19 and Formula 22-23, X1 and X2 are each independently selected from CR x ; Preferably, the R x Each occurrence is identically or differently selected from hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, or a combination thereof.

13. The electroluminescent device according to any one of claims 6 to 11, wherein: In Formula 2-19 and Formula 22-23, X1 is selected from CR x , X2 is N; Preferably, the R x is selected from hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, or a combination thereof.

14. The electroluminescent device according to any one of claims 1 to 13, wherein: The ligand L a Having a structure represented by Formula 20 or Formula 21: Among them, in equation 20 and equation 21, Y is selected from O or S; R x1 , R x2 , R i1 , R i2 , R i3 , R ii1 , R ii2 , R ii3 , R ii4 each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, and combinations thereof; R is selected, at each occurrence, identically or differently, from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted amine having 0 to 20 carbon atoms, and combinations thereof; Preferably, R x1 , R x2 , R i1 , R i2 , R i3 Neutralize and / or R ii1 , R ii2 , R ii3 , R ii4 At least one or two of them are selected, at each occurrence, identically or differently, from deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, or a combination thereof; R is selected from halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, or a combination thereof; More preferably, R x1 , R x2 , R i1 , R i2 , R i3 Neutralize and / or R ii1 , R ii2 , R ii3 , R ii4 At least one or two of them are selected, at each occurrence, the same or different, from substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, or a combination thereof; R is selected from substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, or a combination thereof.

15. The electroluminescent device of claim 14, wherein: R i2 R is selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, or a combination thereof; R is selected from the group consisting of: halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, or a combination thereof; R ii1 , R ii2 , R ii3 , R ii4 At least one or two of the following are selected, at each occurrence, identically or differently, from deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, or a combination thereof; Preferably, R i2 R is selected from the group consisting of: substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, or a combination thereof; R is selected from the group consisting of substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, or a combination thereof; R ii1 , R ii2 , R ii3 , R ii4 At least one or two of the above are selected, at each occurrence, identically or differently, from a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, or a combination thereof.

16. The electroluminescent device according to claim 14 or 15, wherein: In equations 20 and 21, R x1 , R x2 , R i1 , R i2 , R i3 , R ii1 , R ii2 , R ii3 , R ii4 , at least one of R is selected, at each occurrence, identically or differently, from the group consisting of: substituted or unsubstituted alkyl having 3 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, and combinations thereof; Preferably, R x1 , R x2 , R i1 , R i2 , R i3 , R ii1 , R ii2 , R ii3 , R ii4 , at least one of R is selected, at each occurrence, identically or differently, from the group consisting of substituted or unsubstituted alkyl having 3 to 10 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 10 ring carbon atoms, and combinations thereof.

17. The electroluminescent device according to any one of claims 1 to 16, wherein: The metal complex has M(L a ) m (L b ) n (L c ) q structure; Wherein, the metal M is selected from metals with a relative atomic mass greater than 40; L a , L b and L c are the first ligand, the second ligand and the third ligand of the complex respectively; m is 1, 2 or 3, n is 0, 1 or 2, q is 0, 1 or 2, m+n+q is equal to the oxidation state of the metal M; when m is greater than 1, multiple L a The same or different; when n is 2, the two L b The same or different; when q is 2, the two L c Same or different; L a , L b and L c can optionally be linked to form a multidentate ligand; L b and L c Each occurrence is identically or differently selected from the group consisting of: Among them, R a , R b and R c Each occurrence is identical or different and indicates mono-, poly-, or unsubstituted; X b Each occurrence is identically or differently selected from the group consisting of: O, S, Se, NR N1 and CR C1 R C2 ; X c and X d Each occurrence is identically or differently selected from the group consisting of: O, S, Se and NR N2 ; R a , R b , R c , R N1 , R N2 , R C1 and R C2 Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted substituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amine groups, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof; Among them, the adjacent substituent R a , R b , R c , R N1 , R N2 , R C1 and R C2 Can optionally be linked to form a ring.

18. The electroluminescent device of claim 17, wherein the metal M is selected from Ir, Rh, Re, Os, Pt, Au or Cu; preferably, the metal M is selected from Ir, Pt or Os; more preferably, the metal M is Ir.

19. The electroluminescent device according to claim 17 or 18, wherein L b Each occurrence is identically or differently selected from the following structures: wherein R1-R7 are selected, at each occurrence, identically or differently, from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amine groups, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups having 0 to 20 carbon atoms, and combinations thereof; Preferably, at least one or two of R1-R3 are selected from substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, or a combination thereof; and / or at least one of R4-R6 is substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, or a combination thereof; More preferably, at least two of R1-R3 are selected from substituted or unsubstituted alkyl groups having 2-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 2-20 carbon atoms, or a combination thereof; and / or at least two of R4-R6 are selected from substituted or unsubstituted alkyl groups having 2-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 2-20 carbon atoms, or a combination thereof.

20. A consumer product comprising the electroluminescent device of any one of claims 1 to 19.

21. A luminescent material comprising a metal complex, The metal complex comprises a ligand L a , L a Having a structure represented by Formula 1: in, Ring A and Ring B are each independently selected from a five-membered unsaturated carbocyclic ring, an aromatic ring having 6 to 30 carbon atoms, or a heteroaromatic ring having 3 to 30 carbon atoms; R i Each occurrence of R is the same or different, indicating mono-, poly- or unsubstituted; ii Each occurrence is identical or different and indicates mono-, poly-, or unsubstituted; Y is selected from SiR y R y ,GeR y R y , NR y , P.R. y , O, S or Se; When there are two R y When two R y Can be the same or different; X1-X2 are selected from CR in the same or different ways each time they appear x or N; R, R i , R ii , R x and R y Each occurrence is identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted an alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amine group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; Adjacent substituent R i , R x , R y , R and R ii can optionally be linked to form a ring; The metal is selected from metals having a relative atomic mass greater than 40.

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